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. Author manuscript; available in PMC: 2016 Jul 13.
Published in final edited form as: Alkaloids Chem Biol. 2005;61:59–262. doi: 10.1016/s1099-4831(05)61002-4

TABLE I.

Physical-Chemical Properties of Bromotyrosine Derivatives.

1 (3) 5 (7) 6 (7) 14 (15) 17 (16)
Appearance Crystal Colorless crystals Colorless crystals Crystal Crystal
Molecular formula C8H7Br2NO3 C9H9Br2NO3 C9H9Br2NO3
MS m/z 380, 382, 384 [M–MeO]+ (8, 14, 8), 338, 340, 342, [M–BuO]+ (40, 78, 39), 306, 308, 310 [M–MeOH–BuO]+ (14, 27, 18) 394, 396, 398 [M–MeO]+ (1, 1.5, 1), 338, 340, 342 [M–PenO]+ (21, 40, 20), 306, 308, 310[M–MeOH–PenO]+ (12.5, 25, 13) 341, 339, 337 [M]+, 323, 321, 319 [M–H2O]+, 240, 242 [M–H2O–Br]+
MP (°C) 193–195 194–195 166–168 120–121 112–116
[α]D +186° (MeOH) −189° (c 0.5, acetone)
UV λmax (MeOH) nm 257 (8000) 204 (9912) 203 (12134) 231 (3220), 284 (4915)
IR νmax (KBr) cm−1 3445, 3420, 3125, 1700, 1675, 1660, 1650 3410, 3200, 1660 3390, 3185, 1668 3380, 2265, 1635, 1585
15:16 3:1(11) 18 (19) 19 (7) 20 (7) 21 (20)
Appearance Oil Yellow crystals
Molecular formula C8H7Br2NO3 C9H8Br2O4 C12H10Br2O3 C24H24Br4N4O10 C24H24Br4N4O10
MS m/z 323, 325, 327 [M]+, 306, 308, 310 (2), 278, 280, 282 (3), 201, 203, 205 (100) 360, 362, 364 (49, 100, 48), 345, 347, 349 (M–Me, 15, 25, 14), 331, 333, 335 (M-29, 5, 9, 4), 317, 319, 321 (M-43, 36, 70, 35).
MP (°C) 106–108 142–144
[α]D +30° (c 5.7, MeOH) +22° (c 3, MeOH) +152.5° (c 0.92, MeOH) +160.7° (c 0.92, MeOH)
UV λmax (MeOH) nm 254 (4100), 249 (4000) 281 (4900) 207 (6717), 327 (3732) 280 (10600), 231 (17400) 281 (10500), 230 (17500)
IR νmax (KBr) cm−1 3443, 2263, 1710, 1611 3400, 1785 CHCl3 1780 3402, 1728, 1665 3350, 1732, 1662
22:23 (3:1 mixture) (22) 24 (23) 25 (9) 26, 27, 28, 29 mixture (9) 31 (25) 30 (24)
Appearance Oily mixture Sticky semi-solid Sticky semi-solid Colorless needles
Molecular formula C8H7Br2NO3 C8H8BrNO3 C8H8ClNO3 C8H7BrClNO3
MS m/z VG-ZAB, EI 328 (2), 326 (4), 324 (2) (M+1), 327 (6), 325 (12), 323 (6) (M) [calcd for C8H779Br2NO3 322.8790; found 322.8766 ± 0.005], 246 (52) (M-Br), 229 (5), 227 (6) (244-OH), 218 (7), 216 (7) (244-CO), 204 (40), 202 (42) (244-ketone), 176 (24), 174 (24) (202-CO), 95 (17) (174-Br), 43 (100) (O=C=NH) EIMS: 245 (2), 175 (5), 174 (6) EIMS 203 (3), 201 (9, M+), 186 (1), 184 (3, M+–17), 161 (15), 159 (46, M+–CH2CO), 134 (5), 132 (15), 133 (5), 131 (15, M+–C2H2O2), 96 (21), 70 (95), 43 (100, OCNH+) EIMS 283 (4), 281 (14), 279 (11) (four M+) EIMS 219 (1), 217 (3, M+), 203 (12), 201 (35), 191 (2), 189 (7), 174 (4), 172 (11), 159 (33), 157 (100), 182 (13), 136 (15), 123 (19), 59 (52), 44 (46), 43 (35), 39 (40) MS 264, 262 (2.7 each, (M+1)+), 263, 261 (1.4 each, M+), 247, 245 (7 each, ((M+1)–17)+), 246, 244 (1.5 each, M+–17), 235, 223 (23 each, M+–28), 218, 216 (19 each HR: 215.9613 ±0.01 C7H7BrNO2), 204, 205 (5 each, 244–42), 203, 201 (16 each, 244–243) 182 (70 HR: 182.0480 ±0.01 C7H6NO2), 59 (100), 53 (48), 44 (61), 43 (59)
MP (°C) 183–185 165–170
[α]D +0.036° (c 0.084, MeOH)
UV λmax (MeOH) nm 255 (4000), 315 sh (100) 250 (6000), 315 (35) 238 (4100) 250 (2500), 312 (60) 242 (2200) 254 (2600)
IR νmax (KBr) cm−1 (Nujol) 3400–3200, 1700, 1620 (Nujol) 3300, 1680, 1605
43 (35) 44 (35) 45 (35) 46 (35) 67 (21) 51 (40)
Appearance Amorphous white solid Amorphous solid Amorphous solid Amorphous solid Solid Colorless solid
Molecular formula C12H15Br2O3N C13H17Br2O3N C13H18BrO3N C12H16BrO3N C13H12Br2N2O5 C9H11Br2NO
MS m/z HRMS 378.9406 HRMS 333.8839 [M+–NMe3] HRMS 255.9720 [M+–NMe3] HRMS 301.0323 HRMS 433.9094 MS 434, 436, 438 (M+) 348, 350, 352 (M+–C3H4O3N), 318, 320, 322 (M+–C4H6O3N) HRFAB: 307.9279
MP (°C) 220–222
[α]D −1.35° −8.33° −9.00° −15.00° −33° (c 1.1, MeOH)
UV λmax (MeOH) nm (H2O) 287 (1260), 307 (1995), 281 (1250) (H2O) 277 (1263) (H2O) 277 (1260) (H2O) 287 (1257), 307 (1994), 281 (1254) (EtOH) 274 (524), 282 (491) 224 (3.91), 284 (3.08)
IR νmax (KBr) cm−1 (KBr matrix) 3446, 1576 (KBr matrix) 3446, 1576 (KBr matrix) 3446, 1576 (KBr matrix) 3446, 1576 (CHCl)3 3670, 3000, 1760, 1595
48 (38) 207 (41) 52 (42) 54 (44) 55 (45)
Appearance Amorphous solid Colorless amorphous solid Off-white powder Pale yellow semicrystalline solid Colorless oil
Molecular formula C12H18NBr2O C10H11BrN2O3 C11H17Br2N2O C15H24Br2N2O C14H22N2OBr2
MS m/z FABMS 350, 352, 354 EI 288 (6), 286 (6), 200 (99), 199 (13), 198 (100), 187 (32), 185 (32), 120 (20), 101 (10), 77 (11) HREIMS 287.9935 EIMS 354.9 (M++H+4,1), 352.9 (M++H+2,3), 350.9752 (M++H, 2), 324.9 (57), 322.9 (100), 320.9 (61), 294.9 (18), 292.9 (16), 273.0 (88), 271.0 (91), 264.8 (30), 262.8 (16), 81.9 (66), 80.9 (27), 79.9 (68), 78.9 (28) EI 406, 408, 410 (M+–2HCl, 3%; found: 406.025; C15H2479Br2N2O requires 406.0255), 165 (5), 121 (54; found: 121.065; C8H9O requires 121.0653), 85 (64), 58 (100) FAB 407, 409, 411 ([M+–2HCl]+1) EIMS 396, 394, 392 (1:2:1), 352, 349, 347 (1:2:1), 324, 322, 320 (1:2:1), 95, 89, 69, 53, 51, 44 HREIMS 392.0081
MP (°C) 122–123
[α]D
UV λmax (MeOH) nm (EtOH) 277 (1260) (CH3OH) 212 (7762), 281 (1380), 205 (18900) 206 (28000), 284 (600) 293 (400), 448 (440) (MeOH, HCl salt) 218 (12000), 274 (800), 285 (1000)
IR νmax (KBr) cm−1 (Dry film) 2578, 1635 (NaCl film) 3387, 3310, 1651 (NaCl) 3000, 1592, 1473, 1459, 1385, 1261, 865, 739 3000, 2940, 1632, 1454, 1256, 1043 (KBr, HCl salt) 3420, 2950, 1635, 1455, 1260, 1035
56 (45) 57 (46) 58 (46) 60 (49) 59a (47)
Appearance Colorless oil Brown solid White solid Colorless solid Colorless crystalline compound
Molecular formula C14H22N2OBr2 C15H23Br2N2O3 C15H23Br2N2O3 C13H15Br2N3O2 C15H22N2O2Br2
MS m/z (int) EIMS 396, 394, 392 (1:2:1), 353, 351, 349 (1:2:1), 315, 313 (1:1), 87, 69, 58, 44 HREIMS 394.0053 FABMS 437, 439, 441 (1:2:1) HRFABMS 437.0083 FABMS 437, 439, 441 (1:2:1) HRFABMS 437.0090 FAB 404, 406, 408 (1:2:1) (Δ −1.6 mmu) FABMS 421, 423, 425 (1:2:1) HRFABMS 421.010534
MP (°C) 160–162 170–173 148
[α]D
UV λmax (MeOH) nm (MeOH, HCl salt) 214 (14000), 276 (8000), 288 (1100) 207 (37800), 220 (12600), 276 (850 (MeOH, HCl salt) 280 (944), 275 (950), 223 (5769)
IR νmax (KBr) cm−1 (KBr, HCl salt) 3420, 2950, 1635, 1455, 1260, 1035 3300, 2720, 1720, 1620, 1480 3350, 2700, 1725, 1610 (Film) 3200, 3040, 2950, 1680, 1450, 1200, 1130 3328, 2700, 1680, 1580, 1480,
61 (50) 62 (51) 63 (53) 64 (53) 65 (54) 67 (21)
Appearance Amorphous solid Colorless oil Colorless flakes White crystals Colorless crystals Solid
Molecular formula C13H16Br2N3O3 C7H25N2O4Br2 C16H21Br2NO3 C14H18Br2NO3 C13H12N2O5Br2 C13H12Br2N2O5
MS m/z FABMS 420, 422, 424 (1:2:1) HRFABS 419.9568 ESIMS 479, 481, 483 (1:2:1, [M+H]+), 501, 503, 505 (1:2:1, [M+Na]+) HRFABMS 479.0176 EIMS 437 (0.7), 435 (1.4), 356 (1), 354 (1), 167 (1), 149 (1), 86 (8), 84 (2), 73 (3), 71 (3), 58 (100) HREIMS 432.9860 FABMS 410 (46), 408 (94), 406 (61), 325 (11), 323 (24), 321 (14), 307 (8), 305 (19), 303 (10), 244 (12), 58 (100) HRFABMS 407.9641 433.9109 HRMS 433.9094 MS 434, 436, 438 (M+) 348, 350, 352 (M+–C3H4O3N), 318, 320, 322 (M+–C4H6O3N)
MP (°C) 67 193–194 222–225 220–222
[α]D +3.0° (c 0.8, MeOH) +35° (c 0.1, MeOH) +8.9° (c 0.87, MeOH) −33° (c 1.1, MeOH)
UV λmax (MeOH) nm 283 (880) 230 (11200), 282 (9500) 223 (13700), 267 (11000) 275 (480) (EtOH) 274 (524), 282 (491)
IR νmax (KBr) cm−1 (neat) 3365, 3280, 1675, 1453, 1206, 1138 3411, 1630, 1057 (Neat, NaCl) 2920, 2840, 2805, 2758, 1712, 1635, 1195, 950 (Neat, NaCl) 3700–2900, 2940, 2870, 1635, 1565, 930 1748 (sh. 1722, 1703) (CHCl3) 3670, 3000, 1760, 1595
68 (58) 70 (62) 71 (63) 72 (64) 73 (61) 74 (61) 75 (65)
Appearance Plates White powder Colorless glass White powder
Molecular formula C24H26Br4N4O8 C24H27Br4N4O10 C24H26Br4N4O9 C24H24Br4N4O9 C24H24Br4N4O10 C24H24Br4N4O10 C25H26Br4N4O9
MS m/z HRFABMS 850.84 13 (Δ 1.9 mmu) HRFABMS 831.8235 (Δ 0.1 mmu) FABMS 841, 843, 845, 847, 849
MP (°C) 134–137 (dec.) 162–164 174.6–176.6 (dec)
[α]D +252° (acetone) −64.2° (c 0.1, MeOH) +189° (c 0.15) +181.15° (c 2.17, DMSO) +152.5° +160.7°
UV λmax (MeOH) nm EtOH) 234 (4.16), 284 (4.13) 282 (9400), 225 (19000), 202 (34000) 284 (11100), 233 (19750), 205 (18900) (DMSO) 284 (11500), 262 (11600) 280.5 (10600), 231 (17400) 281 (10500), 230.5 (17500) 284 (10500), 232 (19000)
IR νmax (KBr) cm−1 3335, 3160, 1675, 1660, 1580, 1550 3600–3000, 1660, 1600, 1530 3400, 3350 (OH, NH), 1650 (CONH) 3600–3000, 1713, 1665, 1558, 1552, 1435, 1293, 1271, 1131, 1100, 1025 3402, 1728, 1665 3350, 1732, 1662 (KBr matrix) 3450, 1715, 1665
CD N/A N/A N/A N/A N/A N/A 285, +52000 250, +60,200
76 (66) 77 (67) 78 (30) 79 (25) 81 (70)
Appearance Colorless glassy solid NA Colorless solid Amorphous white solid Amorphous white solid
Molecular formula C27H32Br4N4O9 C22H20Br4N4O9 C22H20Br2N4O8 C31H30Br6N4O11 C31H30Br6N4O11
MS m/z FABMS (thioglycerol+MeOH) 875 (1), 873 (2), 871 (4) [M]+, 869 (2), 867 (1), 861 (1.5), 859 (3.5), 857 (5), 855 (3.5), 853 (1.5), 322 (1.5), 320 (2.5), 318 (1.5), 297 (2.5), 295 (4.5). 293 (2.5), 281 (18), 279 (37), 277 (18), 70 (100) HRFABMS 871.97028, found 871.97930 [M]+ FABMS 801, 803, 805, 807, 809 FABMS 629 NA FABMS 1141, 1139, 1137, 1133 ([M+Na]+, 39, 64, 100, 80, 48)
MP (°C) NA NA NA NA NA
[α]D NA NA NA +104° (c 1.67, MeOH) +65.2° (c, 1.04, acetone)
UV λmax (MeOH) nm 234 (9000), 283 (4300) 250 (7850) 260 (0.63), 230 (0.78), 210 (0.90) 283 (10387), 223 (26545) (EtOH) 233 (13500), 283 (2650)
IR νmax (KBr) cm−1 3382, 2357, 1665, 1549, 1106, 603 (KBr matrix) 3360, 1713, 1705, 1660, 1600 NA 3395, 1655, 1602, 1550 3350, 2920, 1655, 1545
CD NA 252, +1.6 344.1 (2.5), 270.3 (13.8), 233.6 (24.1), 199.0 (−25.0) NA NA
82 (71) 83 (63) 84 (72) 85 (72) 86 (65)
Appearance Pale yellow gummy solid Unstable yellow power Powder NA
Molecular formula C31H29Br6N4O11 C31H30Br6N4O9 C31H28Br6N4O10 C31H30Br6N4O10
MS m/z HRFABMS 1112.6897 (Δ 0.6 mmu) EIMS 351 (2), 349 (4), 347 (2), 336 (2), 334 (4), 332 (2), 323 (4), 321 (9), 319, (5), 308 (6), 306 (12), 304 (6), 267 (6), 265 (12), 263 (6) FABMS 1091, 1093, 1095, 1097, 1099, 1101, 1103
MP (°C) NA NA NA NA
[α]D +130° (c 0.1, MeOH) +98.5° (c 0.10, MeOH) +136° (c 0.2, acetone) NA
UV λmax (MeOH) nm 283 (9900), 242(14000), 225 (27000) 284(10400), 257(16000), 224(26000) 280 (3400), 205 (18500) 284 (11000), 232 (19000)
IR νmax (KBr) cm−1 3600–3200, 1720, 1660, 1590, 1525, 3450, 3350 (OH, NH), 1645 (CONH) (Nujol) 3400 br, 1725, 1650, 1590, 1530 (KBr matrix) 3450, 1715, 1665
CD NA NA NA 285, +56500
250, +65200
87 (70) 88 (70) 89:90 (74) 91(75)
Appearance Amorphous off-white powder Amorphous white powder Noncrystalline mixture
Molecular formula C29H26N4O11Br6 C29H26N4O11Br6 C29H26N4O9Br6 C18H18Br4N2O6
MS m/z FABMS 1092, 1090, 1088, 1086, 1084, 1082, (1, 1.8, 1.8, 2, 1.8, 1.8, 1) [M+], 707 (0.8), 705 (1), 703 (0.8), 427 (10), 425 (18), 423 (10) FABMS 1092, 1090, 1088, 1086, 1084, 1082 (<1) [M+], 707 (1), 705 (1), 703 (1), 427 (6), 425 (10), 423 (6) FABMS 1054.68209 [M+H]+ ESIMS 696.7766 [M+Na]+
MP (°C) N/A N/A N/A
[α]D −17.1° (c 1.26, acetone) +50.0° (c 0.27, acetone) +248° (c 0.012, CHCl3)
UV λmax (MeOH) nm (EtOH) 220 (12600), 250 (7740) (EtOH) 215 (12570), 250 (7940)
IR νmax (KBr) cm−1 3360, 2930, 1750, 1660, 1600, 1540, 1260, 1095 3350, 2920, 1700, 1665, 1605, 1540, 1255, 1095, 910
92 (77) 93 (78) 94 (68) 95 (68)
Appearance Brown amorphous solid Yellow powder Amorphous white solid Crystalline
Molecular formula C32H36Br4N10O8 C44H43Br8N6NaO16S C22H21Br4N3O8 C26H25Br4N3O10
MS m/z FABMS 1005, 1007, 1009, 1011, 1013 HRFABMS 1008.9488 FABMS 1583 [M–Na]+, 1503 [M–SO3Na] NA NA
MP (°C) NA 200 (dec.) NA 168–171
[α]D +111.4° (c 0.07, MeOH) −96° (c 0.86, DMSO) +93.5° (c 1.2, MeOH) +122.7° (c 0.44, CHCl3)
UV λmax (MeOH) nm 221 (19600, 279 (9500) 231 (2690), 283 (11900) 284 (5681), 230 (15217) NA
IR νmax (KBr) cm−1 (KBr matrix) 3450, 1665 3700–2500, 1660, 1584, 1541, 1257, 1218, 1183, 1047, 990 3360, 1750, 1660, 1600, 1545 3360, 1750, 1740, 1660, 1600, 1545
CD 245, +60000
285, +50000		 252 (−16.0), 289 (−16.9)
97 (79) 98 (80) 99 (81) 101 (82)
Appearance Colorless oil Amorphous white solid White solid Glass
Molecular formula C10H10Br2N2O4 C10H9Br2NO5 C21H23Br4N3O5 C21H24Br3N3O5
MS m/z EI: 380, 382, 384 (1:2:1) FABMS 938, 940, 942, 944, 946 (1:4:6:4:1) [M+H]+ FABMS 714, 716, 718, 720, 722 (1:4:6:4:1) [M+H]+ HRFABMS 635.9360
MP (°C) 40–42 140–142 NA
[α]D +86° −38° (c 0.73, CHCl3) −70° (c 0.7, MeOH) +21° (c 0.47, CHCl3–MeOH 1:1)
UV λmax (MeOH) nm 228 (8000), 290 (2000) 270 (11650) 283 (9392) (CHCl3) 240 (23000), 287 (16700)
IR νmax (KBr) cm−1 3400, 2940, 1675, 1135, 1120 NA NA (CHCl3–MeOH 1:1) 3690, 3630, 3420, 3020, 2945, 1600, 1570, 1535, 1500, 1465, 1255, 1015
CD 248 (+4.0), 284 (+4.0)
102 (83) 100 (81) 102 (36) 104(36) 105 (78)
Appearance Colorless semisolid Amorphous white solid Colorless solid Colorless solid Colorless fine crystals
Molecular formula C23H25Br4N3O7 C36H51Br4N3O6 C22H24Br4N3O7 C25H29Br4N3O7 C24H27Br4N3O7
MS m/z HRFABMS 797.82940 FABMS 802 (19), 800 (67), 798 (95), 796 (67), 794 (21), 776 (28), 700 (9), 681 (14), 661 (4), 612 (33), 532 (38), 510 (100), 482 (85), 464 (42), 437 (65), 413 (48) FABMS 938, 940, 942, 944, 946 (1:4:6:4:1) [M+H]+ ESI-FTMS 761.8307 (Δ +10.3 mmu) ESI-FTMS 803.8777 (Δ −27.3 mmu) [M+H]+ FABMS (Thiogylcerol matrix) 786, 788, 790, 792, 794 (1:4:6:4:1) [M+H] HRFABMS 785.8661, found 785.8649 [M+H]
MP (°C) NA 40–42 NA NA 154–156
[α]D +69.0° (c 6.4, MeOH) −38° (c 0.73, CHCl3) +96.3° (c 0.19, MeOH) +102° (c 0.067, MeOH) −118° (c 1.02, MeOH)
UV λmax (MeOH) nm 282 (5200), 208 (145000) 270 (11650) (EtOH) 208 (8100), 284 (1200) (EtOH) 207 (8300), 284 (1200) 210 (29500), 283 (7390)
IR νmax (KBr) cm−1 3692–3026, 2933, 2853, 1649, 1643, 1545, 1400, 1384, 1281, 1095, 1044, 988, 918, 868, 765, 739, 704 NA (NaCl) 3251 br, 2935, 1658, 1543, 1456, 1257, 989 (NaCl) 3255 br, 3058, 2933, 1771, 1631, 1542, 1456, 1257, 1024, 987 3700–2300, 1660, 1630, 1540, 1260, 1045
106 (78) 107 (78) 108 (72) 109 (85) 110 (79)
Appearance Colorless fine crystals Colorless powder Powder Colorless amorphous solid Colorless oil
Molecular formula C22H23Br4N3O7 C22H22Br4N3O7S C18H16Br4N2O6 C24H30Br4N3O5 C23H27Br4N3O5
MS m/z FABMS (Glycerol matrix) 758, 760, 762, 764, 766 (1:4:6:4:1) [M+H] HRFABMS 757.8348, found 757.8359 [M+H] FABMS (Glycerol matrix) 836, 838, 840, 842, 844 (1:4:6:4:1) [M–Na]− FABMS (Glycerol–MeOH–H+) 676.8 (0.2%, as the centre of a cluster of ions) [MH+] FABMS (3-nitrobenzyl alcohol) 698.6 (1.0% as the centre of a cluster of ions) [MNa+], 658.6 (1.1% as a quintet) [MH+–H2O] FABMS 764, 762, 760, 758, 756 [M+], 748, 746, 742, 740, 684, 682, 680, 678, 602, 600, 658 HRFABMS 759.8892 FABMS 742, 744, 746, 748, 750 (1:4:6:4:1) [M++H] HRFABMS 745.8721 [M+4+H]+, found 745.8776
MP (°C) 154–157 190 73–75 NA NA
−97° (c 0.58, MeOH) −69° (c 0.19, MeOH) +110° (c 0.2, acetone) −4.5° (c 1.3, MeOH) +6.6° (c 0.75, MeOH)
UV λmax (MeOH) nm 207 (45400), 283 (7300) 206 (53200), 220 (25000 sh), 282 (6760) 281 (6900), 207 (39200) 220 (10000), 284 (1000) 277 (1700), 284 (1400)
IR νmax (KBr) cm−1 3700–2300, 1660, 1635, 1540, 1260, 1045 3700–2500, 1662, 1596, 1541, 1258, 1217, 1046 (Nujol) 3350 br, 1660, 1590, 1540, 1270, 1220, 1095 3450, 2980, 2880, 1690, 1470, 1400, 1220, 1150 3400, 2940, 2845, 1670, 1520, 1470, 1135, 1120
111 (79) 112 (86) 113 (69) 114 (69) 116 (79) 117(79)
Appearance Colorless oil Colorless oil NA NA Colorless oil Colorless oil
Molecular formula C23H27Br4N3O5 C22H25Br4N3O5 C15H16Br2N4O4 C16H19Br2N5O4 C15H17Br2N5O4 C15H17Br2N5O5
MS m/z FABMS 742, 744, 746, 748, 750 (1:4:6:4:1) [M++H] HRFABMS 745.8721 [M+4+H]+, found 745.8729 ESIMS 726.85, 728.85,730.85, 732.86,734.85 [M+H]+ HRESIMS 728.8676 (Δ 0.8 mmu) [M+H]+ FABMS 475, 477, 479 [MH+] FABMS 504, 506, 508 [MH+] FABMS 490, 492, 494 (1:2:1) [M++H] HRFABMS 491.9705 [M+2+H]+, found 491.9682 FABMS 506, 508, 510 (1:2:1) [M++H] HRFABMS 507.9654 [M+2+H]+, found 507.9672
MP (°C) NA NA NA NA NA NA
[α]D +9.1° (c 0.39, MeOH) NA +187° (c 2.0, MeOH) +139° (c 1.9, MeOH) +24° (c 0.98, MeOH) +26° (c 0.38, MeOH)
UV λmax (MeOH) nm 277 (1700), 284 (1400) 280 (3.28) NA NA 277 (1700), 284 (1400) 231 (6300), 284 (2400)
IR νmax (KBr) cm−1 3400, 2940, 2850, 1675, 1470, 1200, 1135, 1120 1736, 1655, 1591, 1542, 1458, 1390, 1257, 1044, 737 NA NA 3400, 2930, 2845, 1680, 1540, 1430, 1200, 1135 3400, 2920, 2850, 1670, 1540, 1430, 1200, 1135, 1125
119 (89) 120 (83) 121 (90) 122 (91) 123 (89)
Appearance NA Colorless oil NA Colorless amorphous solid NA
Molecular formula C15H18Br2N5O4 C16H18Br2N5O4 C24H22O8N6Br2 C27H29Br4N7O7 · HCl C27H32Br4N7O6
MS m/z FABMS 490, 492 494 [MH+] HRFABMS 503.97073 FABMS 506 (53), 504 (100), 502 (55), 307 (5), 154 (50) FABMS 681, 683, 685 (1:2:1) HRFABMS 680.9940 FDMS 880, 882, 884, 886, 888 (1:4:6:4:1) FABMS 866, 868, 870, 872, 874 [MH+]
MP (°C) NA NA NA NA NA
[α]d −158° (c 1.0, MeOH) +121.9° (c 5.7, MeOH) NA −85° (c 2.10, MeOH) −10° (c 1.0, MeOH)
UV λmax (MeOH) nm 220 (4.47), 284 (4.08) 266 (13100), 226 (13700) NA NA 220 (4.54), 228 (4.11)
IR νmax (KBr) cm−1 3400, 1680, 1543, 1437, 1381, 1250 3654–3000, 2937, 1660, 1595, 1543, 1435, 1273, 1219, 1047, 1025, 997, 824, 765 NA NA 3375, 1680, 1543, 1456, 1387, 1250
124 (83) 125 (79) 126 (66) 127 (92) 128(92)
Appearance Colorless semisolid Colorless oil Colorless glassy solid NA NA
Molecular formula C16H24Br2N5O4 C15H21Br2N5O4 C15H7D7 Br2N5O5 C16H19Br2N3O7 C16H19Br2N3O7
MS m/z HRFABMS 510.01640 FABMS 512 (25), 510 (50), 508 (25), 451 (7), 273 (22), 219 (12), 154 (100) FABMS 494, 496, 498 (1:2:1) [M++H] HRFABMS 496.0018 [M+4+H]+, found 496.0035 FABMS (Thioglycerol) 518 [M+7D–7H]+ (13), 513 [M+2D–2H]+ (4), 496 (8), 478 (6), 295 (23), 279 (22), 157 (60), 71 (100) HRFABMS 518.20911 [M+7D–7H]+ ESIMS 524, 526, 528 (1:2:1) [M+H]+ ESIMS 524, 526, 528 [M+H]+
MP (°C) NA NA NA NA NA
[α]D +47.0° (c 7.9, MeOH) +27° (c 0.18, MeOH) NA NA NA
UV λmax (MeOH) nm 284 (2500), 218 (4600) 228 (8600), 290 (3400) 232 (9100), 283 (4250) 229 (18500), 280 (10600) 227 (19000), 281(10500)
IR νmax (KBr) cm−1 3588–3050, 3024, 2782, 1658, 1402, 1024, 992 3400, 2920, 1660, 1520, 1470, 1210 3500–3000, 2928, 2860, 1690–1630, 1405, 1100, 605 3450, 1730, 1715, 1665 3450, 1730, 1715, 1665
129 (94) 130 (94) 131 (95) 132 (96)
Appearance Colorless glass Colorless glass Glass Colorless oil
Molecular formula C21H23Br4N3O6 C21H23Br4N3O7 C22H25Br4N3O7 C36H51Br4N3O8
MS m/z EIMS 406 (0.4), 404 (0.4), 402 (0.4), 3.62 (1), 360 (2), 358 (2), 356 (1), 323 (1), 321 (2), 319 (2), 281 (2), 280 (7), 279 (6), 278 (17), 277 (4), 276 (4), 268 (1), 267 (4), 266 (2), 265 (6), 264 (1), 263 (7), 248 (5), 246 (3), 200 (6), 198 (4), 58 (100). CIMS 407, 405, 403, 361, 359, 281, 279, 277, 275, 249, 247, 233, 231, 221, 219, 193, 191, 166, 164, 125, 123, 121 EIMS 523 (9), 521 (27), 519 (26), 517 (8) overlapping 2 Br clusters, 477 (3), 475 (4), 473 (2) 2 Br cluster, 441 (6), 439 (13), 437 (6) 2 Br cluster, 423 (5), 421 (11), 419 (4) 2 Br cluster, 407 (3), 405 (4), 403 (2) 2 Br cluster, 393 (11), 391 (39), 358 (2), 356 (6), 354 (2), 283 (8), 281 (16), 279 (12), 278 (9), 276 (20), 274 (18), 272 (8) 2 Br cluster, 249 (94), 247 (97) 1 Br cluster, 235 (16), 233 (14) 1 Br cluster, 221 (24), 219 (27) 1 Br cluster, 207 (11), 205 (24), 203 (16) 2 Br cluster, 196 (9), 194 (100), 192 (17), 179 (9), 177 (18), 175 (8), 169 (4), 167 (19), 155 (45), 127 (38), 125 (43), 113 (9), 111 (12). CIMS 441, 439, 437 (2 Br), 407, 405, 403 (2 Br), 340, 338, 336 (2 Br), 249, 247 (1 Br), 221, 219 (1 Br). HRFDMS 749.8308 (M+H, C21H2479Br281Br2N3O7, calcd 749.83068) HRFABMS 763.8499 HRFABMS 974.0468 [M+H]
[α]D −65.2° (c 0.52, MeOH) −60.2° (c 0.63, MeOH) −57.1° (c 0.014, MeOH) −71.4° (c 2.8, acetone)
UV λmax (MeOH) nm 229 (12700), 262 (7100 sh), 276 (4650 sh), 283 (3200 sh) 218 (28600), 256 (7000 sh), 262 (6400 sh), 277 (4000 sh), 282 (3000) 218 (17600), 255 (6700 sh), 279 (3000 sh) 210 (50900), 224 (27600 sh), 258 (10400 sh)
IR νmax (KBr) cm−1 (CHCl3) 3420, 2950, 1675 s, 1660, 1540–1530, 1460, 1260, 1150, 1120, 910 (CHCl3) 3420, 2940, 1670 s, 1620, 1590, 1530 s, 1450, 1250, 1140, 1110, 900 (KBr smear) 3362, 2925, 2851, 1668, 1652, 1558, 1540, 1456, 1258, 1197, 1146, 1118, 1044, 1024 (CHCl3) 3430, 3390, 2910, 2830, 1660, 1570, 1445, 1135, 1105, 1030, 980, 950, 890
133 (96) 134 (97) 135 (98) 136 (98)
Appearance Bright yellow oil NA Colorless solid Colorless solid
Molecular formula C27H25Br4O8 C22H25O6Br4N3 C22H23Br4N3O7 C35H51Br4N3O7
MS m/z FABMS 994.4 [M+H+C4H10O2S2], 840.0 [M+H]. HRFABMS 993.8563 [M+H+C4H10O2S2] FABMS [M+H]+ 752 (22), 750 (57), 748 (100), 746 (71), 744 (23), 393 (26) FABMS (positive, glycerol matrix) 758, 760, 762, 764, 766 [M+H]+, 780, 782, 784, 786, 788 [M+Na]+ HRFABMS 783.8152 (calcd for C22H2379Br281Br2N3O7Na, Δ +2.6 mmu) FABMS (Positive, NBA matrix) 954, 956, 958, 960, 962 [M+H]+, 976, 977, 980, 982, 984 [M+Na]+ HRFABMS 980.0320 (calcd for C36H5179Br281Br2N3O7Na, Δ −0.4 mmu)
MP (°C) NA NA NA
[α]D −80.3° (c 0.3, acetone) −62.3° (c 1.2, MeOH-CH2Cl2) −89.7° (c 0.146, MeOH) −53.5° (c 0.263, acetone)
UV λmax (MeOH) nm 208 (53400), 224 (33300 sh), 298 (25000) NA (EtOH) 207 (64200), 218 (28900 sh), 255 (11000 sh) (EtOH) 207 (51100), 219 (22700 sh), 255 (9000 sh)
IR νmax (KBr) cm−1 (CHCl3) 3380, 2910, 1700, 1640, 1610, 1445, 1145, 1105, 1035, 985, 950, 880 (Neat) 3450, 3300, 1660 s, 1620, 1590, 1260 (Film) 3300, 2930, 1660, 1530, 1450, 1380, 1260, 1110, 760 (Film) 3320, 2920, 2850, 1650, 1540, 1450, 1250, 1120
137 (99) 138 (100) 139 (101) 140 (33) 141 (102)
Appearance NA Oil Yellow semisolid, oil NA Colorless amorphous solid
Molecular formula C15H17N5O3Br2 C15H16N4O3Br2 C15H18N4O3Br C14H15BrN4O3 C31H48N6O4Br2
MS m/z EIMS 477, 475, 473 EIMS 351, 149, 247 (2.5, 5, 2.5), 335, 333, 331 (2.5, 5, 2.5), 307, 305, 303 (50, 100, 50), 292, 290, 288 (20, 40, 20), 195 (22), 181 (31), 137 (30), 81 (80) FABMS 381 (92), 383 (100) [M+H]+, 403 (36), 405 (38) [M+Na]+ HRFABMS 381.0573 FAMS 367, 369 SIMS 727, 729, 731 (1:2:1)
MP (°C) 113–115 NA NA NA 94–95
[α]D NA NA NA NA NA
UV λmax (MeOH) nm NA 207.5 (44140) 388 (630), 289 (sh 2660), 280 (3040), 206 (33600) 387 (620), 289 (2600), 278 (3020), 207 (31000) 284 (970)
IR νmax (KBr) cm−1 1538, 1372, 1107 3271, 1652, 1471, 1260 3390 br, 3231 br, 2936, 2837, 1655, 1495, 1254, 1054 3151, 1675 2930, 2850, 1675, 1520, 1450, 1250
142 (102) 143 (102) 144 (103) 145 (103)
Appearance Colorless amorphous solid Colorless amorphous solid Colorless amorphous solid Colorless amorphous solid
Molecular formula C32H50N6O4Br2 C33H52N6O4Br2 C34H53N6O4Br2 C36H59N6O4Br2
MS m/z SIMS 741, 743, 745 (1:2:1) SIMS 755, 757, 759 (1:2:1) FABMS 767, 769, 771 (1:2:1) [M+H]+ HRFABMS 767.2540 FABMS 797, 799, 801 (1:2:1) [M+H]+ HRFABMS 767.2956
MP (°C) 93–95 108–110 NA NA
[α]D NA NA NA NA
UV λmax (MeOH) nm 284 (930) 284 (910) 284 (1100), 274 (1400) 284 (710), 274 (1000)
IR νmax (KBr) cm−1 2930, 2850, 1675, 1540, 1455, 1260 2930, 2860, 1675, 1520, 1450 3400, 2910, 1675, 1625, 1535, 1450, 1250, 1120 3400, 2840, 1675, 1620, 1535, 1450, 1200, 1130
146 (104) 147 (105) 148 (103) 149 (79) 150 (79)
Appearance Colorless amorphous solid NA Colorless oil Colorless oil Colorless oil
Molecular formula C17H23O3N6Br2 C22H25N6O3Br2 C14H15Br2N6O3 C15H18Br2N5O4 C15H17Br2N4O4
MS m/z FABMS (Positive glycerol matrix) 559, 557, 555 (1:2:1) [M+K]+, 521, 519, 517 (1:2:1) [M+H]+, 505, 503, 501 (1:2:1) [M+H–NH2]+, 441, 439 (1:2:1) [M–Br]+ HRFABMS 517.0241 FABMS 579, 581, 583 (1:2:1) HRFABMS 581.0366 (Δ 3.1 mmu) 459.9631 FABMS 490, 492, 494 (M++H, 1:2:1) HRFABMS 491.9705 FABMS 475, 477, 479 (M++H, 1:2:1) HRFABMS 476.9596
MP (°C) NA NA NA NA NA
[α]D NA NA NA NA NA
UV λmax (MeOH) nm 277 (520) 286 (800), 269 (shoulder), 260 (2900), 217 (15300) 277 (1700), 284 (1400) 277 (1700), 284 (1400) 235 (2600), 290 (2800)
IR νmax (KBr) cm−1 (Film) 3400, 1680, 1540, 1435, 1200, 1140 3400, 1680, 1200, 1140 3400, 2920, 2845, 1680, 1520, 1470, 1200, 1135, 1120 3400, 2920, 1680, 1520, 1470, 1200, 1135, 1120 3400, 2920, 2845, 1680, 1520, 1135, 1120
151 (89) 152 (107) 153 (107) 154 (109) 155 (110)
Appearance NA White powder White powder Colorless foam Oil
Molecular formula C18H26Br2N5O2 C22H24Br2N4O6S2 C22H24Br2N4O6S2 C44H46Br4N8O12S4 C8H17N2O4S2
MS m/z 502.0432 FABMS 689 (5), 687 (15), 685 (7) [M++Na], 667 (62), 665 (100), 663 (50) [M++H] HRFABMS 664.9560 NA NA EIMS 268 (18) [M+], 193 (60), 134 (60) [M+–SCH2CH2NHCOOMe], 102 (100) [M+–SSCH2CH2NHCOOMe] CIMS (isobutane) 269 (100) [M++H], 237 (18), 197 (5), 134 (80), 102 (8) HRFABMS 269.0626 (Δ 0.4 mmu)
MP (°C) NA 172–174 NA NA NA
[α]D +17° (c 1.0, MeOH) NA NA 0° (c 1.0, MeOH) NA
UV λmax (MeOH) nm 285 (3.17), 330 (2.69) (EtOH) 277 (4875) NA 212 (110,000), 290 (14,100) NA
IR νmax (KBr) cm−1 3406, 1680, 1556, 1475, 1262 3348, 1657, 1637, 1536, 1025, 679 3300 br, 1670, 1540 3400–3100 br, 2900, 1670, 1570, 1450, 1200, 1025 3630, 3547, 2960, 1724, 1630, 1525, 1255, 1052
156 (110) 157 (110) 158 (110) 159 (112) 160 (112)
Appearance Oil Oil Oil NA NA
Molecular formula C12H13N3O3BrS C11H15N3O5BrS C15H20N3O5BrS2 C15H19N4O5S2Br C15H18N3O6S2Br
MS m/z EIMS 357/359 (3) [M+], 328/330 (5) [M+–HCN–2H], 298/300 (5) [M+–HSCN], 281/283 (7), 211/213 (100) [C8H6NOBr], 59 (30) [HSCN]. CIMS (isobutane) 358/360 (21) [M++H], 329/331 (29) [M+–HCN–H], 299/301 (35) [M+–HSCN+H], 283/285 (25). HRFABMS 357.9856 (Δ 0.5 mmu) EIMS 379/381 (4) [M+], 363/365 (2) [M+–NH2], 211/213 (100) [C8H6NOBr]. CIMS (isobutane) 380/382 (32) [M++H], 364/366 (20) [M+–NH2+H], 301/303 (15) [M+–SO2NH2+2H]. HRFABMS 379.9913 (Δ 0.3 mmu) EIMS 465/467 (5) [M+], 390/392 (1) [M+–NHCOOMe–H], 331/333 (22) [M+–SCH2CH2NHCOOMe], 299/301 (37) [M+–SSCH2CH2NHCOOMe], 226/230 (40), 211/213 (31) [C8H6NOBr]. CIMS (isobutane) 466/468 (10) [M++H], 375/377 (3), 333/335 (8), 299/301 (35). HREIMS 465.0030 (Δ 0.2 mmu) HRFABMS 479.0094 [M+H]+ (Δ −3.5 mmu) HRFABMS 501.9724 [M+H]+ (Δ 0.6 mmu)
[α]D NA NA NA NA NA
UV λmax (MeOH) nm 280 (5450) NA NA 206 (18070), 284 (1858) 206 (25935), 280 (2057)
IR νmax (KBr) cm−1 3627, 3541, 2257, 2157, 1678, 1634, 1442, 1378, 1040 3300 br, 1670, 1540 3630, 3547, 2960, 1724, 1630, 1525, 1255, 1052 (Film) 3500–3100 br, 3327, 1668, 1539, 1420, 1358, 1287, 1221, 1010, 985 (Film) 3600–2600 br, 1647, 1527, 1424, 1390, 1287, 1219, 1047, 1019, 985
161 (112) 162 (112) 163 (112) 164 (112) 165 (114)
Appearance NA NA NA NA Pale yellow amorphous solid
Molecular formula C15H20N5O5S2Br C16H22N3O5S2BrNa C12H15N2O5S2Br C22H24N4O7S2Br2 C25H34Br2N7O6S2
MS m/z HRFABMS 494.0055 [M+H]+ (Δ 3.4 mmu) HRFABMS 502.0102 [M+Na]+ (Δ 2.0 mmu) HRFABMS 400.9795 [M+Na]+ (Δ 1.2 mmu) HRFABMS 700.9396 [M+Na]+ (Δ 4.5 mmu) (+)-HRFABMS 752.0381 for C25H34Br2N7O6S2 (Δ −2.3 mmu) (−)-HRFABMS 742.8976 for C22H23Br2N4O9S2 (Δ −0.3 mmu) ESIMS 743
MP (°C) NA NA NA NA 76–80
[α]D NA NA NA NA NA
UV λmax (MeOH) nm NA NA NA NA 204 (4.73), 281 (3.88)
IR νmax (KBr) cm−1 (Film) 3600–2600 br, 1666, 1631, 1596, 1531, 1437, 1408, 1354, 1290, 1220, 1145, 1043. 1025, 996 (Film) 3500–3000 br, 1660, 1531, 1419, 1384, 1360, 1260, 1231, 1037, 985 (Film) 3600–3000 br, 1654, 1531, 1501, 1420, 1361, 1284, 1043, 973 3600–2900 br, 1660, 1625, 1531, 1502, 1449, 1425, 1361, 1287, 1284, 1213, 1149, 1044 3400 br, 2925, 1655, 1530, 1485, 1250, 1230, 1040
166 (114) 167 (114) 168 (114) 168a (114) 169 (117)
Appearance Pale yellow amorphous solid Yellow amorphous solid Yellow amorphous solid White solid White amorphous solid
Molecular formula C25H32Br2N7O12S4 C31H27Br3N4O13S3 C31H26Br3N4O13S3 C36H37Br3N4O10S2 C22H24N4O6S3Br2
MS m/z HRFABMS 909.9285 (+)–FABMS 1068.8/1066.8, 1046.8/1044.8, 944.8/942.8 [M-SO3+Na+2H]+ (−)-FABMS 1044.9/1042.9 [M+2Na–H]−, 1022.9/1020.9 [M+Na]− (+)–HRFABMS 1068.7794 [M+3Na]+, 1046.8165 [M+2Na+H]+ (+)–FABMS 1044.7/1042.7, 1022.6/1020.6 [M+Na+H]+, 942.8/940.8 [M–SO3+Na+H]+ (−)-FABMS 998.7/996.8 ESIMS 998.7/996.8 (+)–HRFABMS 1044.8008 [M+2Na]+ HRFABMS 990.9545 [M+H]+ ESIMS 695 (46), 697 (100), 699 (60) [M+H]+, 717 (35), 719 (74), 721 (45) [M+Na]+, 466 (19), 468 (20), 363 (19), 365 (22) MALDI-TOFMS 718.9037 [M+Na]+
MP (°C) 155–160 191–194 236–239 136–138 NA
[α]D NA NA NA NA NA
UV λmax (MeOH) nm 204 (4.60), 281 (3.98) 204 (4.83), 291 (4.11) 205 (4.88), 280 (3.93) NA NA
IR νmax (KBr) cm−1 3400 br, 2930, 1660, 1530, 1485, 1230, 1040 3400 br, 2925, 1660, 1565, 1270, 1230, 1040 3400 br, 2925, 1655, 1540, 1385, 1270, 1235, 1045 NA NA
170 (117) 171 (117) 172 (44) 173 (118) 174 (118)
Appearance White amorphous solid Yellow oil Pale tan semicrystalline solid White semicrystalline solid White semicrystalline solid
Molecular formula C22H23N4O6S2Br3 C44H46N8O12S4Br4 C23H28Br3N3O4 C21H24Br3N3O4 C21H23Br4N3O4
MS m/z ESIMS 741 (25), 743 (81), 745 (100), 747 (35) [M+H]+ MALDI-TOFMS 766.8495 [M+Na]+ ESIMS 1323 (8), 1325 (38), 1327 (52), 1329 (43), 1331 (15) [M+H]+, 1345 (13), 1347 (54), 1349 (100), 1351 (77), 1353 (25) [M+Na]+ MALDI-TOFMS 1348.9407 [M+Na]+ EIMS 647, 649, 651, 653, (M+–HCl. 5%), 631, 633, 635, 637 (4), 562, 564, 566, 568 (9), 484, 486, 488 (5), 404, 406 (2), 225, 227 (35), 58 (100) FABMS 648, 650, 652, 654 ([M+–HCl]+1) FABMS 619.9380 [M+H]+ FABMS 699.8480 [M+H]+
MP (°C) NA NA 87–88.5 NA NA
[α]D NA NA NA NA NA
UV λmax (MeOH) nm NA NA 294 (3286), 266 (3850), 260 (4000), 250 (8300), 215 (26100) 222 (16700), 280 (3100) 222 (17400), 274 (2100)
IR νmax (KBr) cm−1 NA 3369, 1655, 1534, 1490, 1426, 1228, 1016, 669 3427, 2922, 1632, 1454, 1256, 1053 3350, 2940, 1655, 1620, 1530, 1490, 1455 3400, 2990, 1670, 1630, 1530, 1460
175 (118) 176 Acetate (119) 177 Acetate (119) 178 (82) 179 (121)
Appearance Colorless gum NA NA Glass NA
Molecular formula C36H52Br3N3O5 C21H25Br2N3O4 C21H24Br3N3O4 C21H24Br3N3O4 C20H23Br2N3O3
MS m/z HRFABMS 844.1459 [M+H]+ FABMS 588 (4), 586 (7), 584 (4) [M+H]+, 572 (5), 570 (8), 568 (5), 492 (4), 490 (4), 343 (11), 341 (10), 301 (9), 299 (9), 228 (19), 226 (21), 201 (47), 199 (57) FABMS 668 (2), 666 (4), 664 (4), 662 (2) [M+H]+, 652 (2), 650 (4), 648 (4), 646 (2), 586 (2), 584 (1), 572 (3), 570 (4), 568 (3), 492 (1), 490 (1), 343 (8), 341 (7), 308 (2), 306 (2), 304 (3), 281 (8), 279 (13), 277 (7) EIMS 409 (13), 407 (33), 405 (13), 307 (20), 305 (45), 303 (23), 292 (18), 290 (29), 288 (16), 187 (40), 185 (54), 183 (38), 181 (32) HRFABMS 619.9377 HRFABMS 514.0178 [M+H]+
MP (°C) NA NA NA NA NA
[α]D NA NA NA NA NA
UV λmax (MeOH) nm 214 (18500), 222 (17200), 282 (2700) NA NA (CHCl3) 240 (6750), 280 (3500) 280 (834)
IR νmax (KBr) cm−1 3400, 2910, 1660, 1645, 1490, 1445 NA NA [CHCl3–MeOH (1:1)] 3410, 3015, 2930, 1670, 1605, 1530, 1495, 1470, 1420 (Film) 1658, 1540, 1458, 1420, 1258, 1200, 1010
180 (121) 181 (121) 182 (121) 182 (121) 183 (121)
Appearance NA NA NA NA NA
Molecular formula C20H24BrN3O3 C25H26Br2N3O3 C20H23Br2N3O3 C21H25Br2N3O3 C20H22Br3N3O4
MS m/z HRFABMS 434.1086 [M+H]+ HRFABMS 578.0306 [M]+ HRFABMS 512.0141 [M+H]+ HRFABMS 526.0292 [M+H]+ HRFABMS 609.9254 [M+H]+
MP (°C) NA NA NA NA NA
[α]D NA NA NA NA NA
UV λmax (MeOH) nm 280 (641) 250 (5600) 282 (512) 282 (600) 282 (2600)
IR νmax (KBr) cm−1 (Film) 1680, 1540, 1498, 1458, 1200, 1138, 840, 800 (Film) 1670, 1200, 1130, 800 (Film) 1678, 1200, 1138, 840, 800 1678, 1204, 1140, 840, 800 1678, 1204, 1140, 800
185 (121) 186 (121) 187 (121) 188 (121) 189 (86) 190 (122)
Appearance NA NA NA White powder Colorless oil White solid
Molecular formula C21H24Br3N3O4 C21H24Br3N3O4 C22H26Br3N3O4 C9H9NO3 C23H28Br3N3O5 C24H28N3O6Br3
MS m/z HRFABMS 619.9391 [M+H]+ HRFABMS 619.9349 [M+H]+ HRFABMS 639.9457 [M+H]+ NA ESIMS 663.97, 665.96, 667.98, 669.96 [M+H]+ HRESIMS 663.9763 [M+H]+ (Δ 2.3 mmu) FABMS 692, 694, 696, 698, (1:2:2:1) [M+H]+ HRFABMS 694.2150 [M+H]+ (Δ −2.2 mmu)
MP (°C) NA NA NA NA 190–195
[α]D NA NA NA NA NA
UV λmax (MeOH) nm 282 (2800) 280 (2000) 280 (1800) 280 (3.26) 217 (3.65), 280 (4.78)
IR νmax (KBr) cm−1 1680, 1400, 1200, 800 1678, 1202, 1138, 842, 800, 722 1670, 1200, 1135, 838, 798, 721 1694, 1650, 1600, 1480, 1452, 1430, 1282, 1200, 1132, 1120, 1072, 1020, 920, 890, 740, 688 2937, 2852, 1743, 1656, 1533, 1493, 1452, 1253, 1047, 739 3404, 2926, 1675, 1494
191 (122) 192 (84) 192 (123) 194 (123) 195 (124)
Appearance White solid Colorless amorphous solid Yellow amorphous solid Yellow amorphous solid White powder
Molecular formula C22H26N3O4Br3 C23H29O4N4Br4 C28H31Br4N4O4 C28H31Br4N4O4 C24H31N3Br4O3 · HCl
MS m/z FABMS 633, 635, 637, 639 (1:2:2:1) [M+H]+. HRFABMS 635.7964 (Δ −2.8 mmu) FABMS 771, 769, 767, 765, 763 [M+Na]+, 749, 747, 745, 743, 741 [M+H]+, 669, 667, 665, 663 HRFABMS 744.8868 FABMS (glycerol matrix) 803, 805, 807, 809, 811 [M]+; 645, 647, 649; 466, 468, 470; 411, 413, 415; 347, 349, 351 HRFABMS 806.9037 [M]+ (Δ 0.0 mmu) FABMS 803, 805, 807, 809, 811 [M]+; 645, 647, 649; 466, 468, 470; 426. 428. 430; 409, 411, 413 HRFABMS 806.9007 [M]+ (Δ −3.1 mmu) DEIMS 726, 728, 730, 732, 734 (1.7); 448, 450, 452 (25:50:25); 403, 405, 407 (10:15:10); 320, 322, 324 (50:100:50)
MP (°C) 175–178 NA NA NA 200
[α]D NA NA NA NA +5.1° (c 0.013, MeOH)
UV λmax (MeOH) nm 214.5 (5.12), 280.0 (4.02) 210 (23000), 285 (1600) 216 (21800), 258 (4000 sh) 214 (20600), 258 (3800 sh) 283 (7800), 276 (9400), 245 (12300)
IR νmax (KBr) cm−1 3350, 1670, 1200, 1137, 720 3400, 3100, 1680, 1400, 1200, 1130 NA NA (CHCl3) 3350, 1645, 1535, 1515, 1470, 1450, 1240, 980
196 (125) 197 (125) 198 (125) 199 (90)
Appearance Pale orange oil Colorless amorphous solid Colorless, amorphous solid NA
Molecular formula C25H33Br4N3O3 C23H31N3O3Br3 C24H33N3O3Br3 C17H26N6O3Br2
MS m/z CIMS 740 (22), 742 (70), 744 (100), 746 (64), 748 (20) [MH+]; 696 (1), 698 (5), 700 (7), 702 (4), 704 (1) [MH+–NMe2]; 662 (4), 664 (10), 666 (8), 668 (2) [MH+–Br]; 582 (3), 584 (6), 586 (3) [MH+–Br2]; 462 (3), 464 (12), 466 (12), 468 (3), 334 (15), 336 (26), 338 (15) [C11H14Br2NO+]; 309 (12), 311 (21), 313 (8), 118 (22). EIMS 696 (1), 698 (3), 700 (7), 702 (3), 704 (1) [MH+–NMe2]; 462 (4), 464 (9), 466 (7), [C17H26Br2N3O2+]; 377 (5), 379 (6), 381 (3) [C12H15Br2N2O2+]; 334 (52), 336 (99), 338 (50) [C11H14Br2NO+]; 256 (20), 258 (15) [C11H14BrNO+]; 84 (17), 58 (100) [CH2NMe2+] FABMS 634, 636, 638, 640 (1:3:3:1) [M+H]+ HRFABMS 633.9944 FABMS 648, 650, 652, 654 (1:3:3:1) [M+H]+ HRFABMS 648.0092 FABMS 521, 523, 525 (1:2:1) HRFABMS [MH+] 521.0501
MP (°C) NA 64–67 79–81 NA
[α]D 0° (c 5.0, CHCl3) +21° (c 1.0, MeOH) +16° (c 1.0 MeOH) NA
UV λmax (MeOH) nm NA 281 (2400) 281 (2900) NA
IR νmax (KBr) cm−1 1036, 1211, 1221, 1259, 1473, 1545, 1678, 2450, 2969, 3023, 3222 3425, 1655 3425, 1655 NA
200 (79) 201 (127) 202 (127) 203 (127)
Appearance Colorless oil White needles White needles Colorless gum
Molecular formula C5H22Br2N5O4 C29H41I3N4O4 C29H40I4N4O4 C28H39I3N4O4
MS m/z FABMS 494, 496, 498 (1:2:1) [M++H] HRFABMS 496.0018 FABMS 891 (100) [MH+], 643 (18), 517 (10), 430 (93), 391 (12), 304 (93). EIMS 890 (Not observed) [M], 643 (10), 517 (10), 430 (25), 304 (35), 254 (56), 142 (100), 127 (92) FABMS 1017 (87) [MH +], 643 (18), 430 (100), 391 (12), 307 (45). EIMS 1016 (Not observed) [M], 643 (30), 430 (50), 304 (100), 254 (10) FABMS 877 (100) [MH +], 629 (13), 503 (17), 430 (100), 329 (10), 290 (37). EIMS 876 (Not observed) [M], 629 (45), 503 (15), 430 (100), 304 (12), 290 (11), 142 (40), 127 (15)
MP (°C) NA 135–137 114–116 NA
[α]D NA −0.23° (c 0.51) −0.20° (c 0.35) −0.74° (c 0.24)
UV λmax (MeOH) nm 235 (2600), 287 (700) 211 (25000), 223 (24000), 273 (5400) 207 (32000), 221 (35000), 275 (8400) 210 (40000), 222 (39000), 278 (9200)
IR νmax (KBr) cm−1 3400, 2920, 2850, 1680, 1635, 1135, (CHCl3) 3368, 2935, 2883, 2855, 1672, 1600, 1518, 1500, 1491, 1479, 1463, 1447, 1441, 1416, 1278, 1272, 1254, 1050, 1020, 996 (CHCl3) 3368, 2938, 2882, 2855, 1674, 1614, 1602, 1522, 1464, 1416, 1264, 996 (CHCl3) 3367, 2940, 2861, 1671, 1522, 1492, 1463, 1264, 1260, 1255, 1050, 996, 925
204 (129) 205 (129) 206 (129) 227 (129) 208 (129)
Appearance Colorless foam Colorless foam Pale yellow foam White powder Yellow needles
Molecular formula C34H30Br4N4O8 C34H29Br5N4O8 C34H30Br4N4O8 C34H29Br4N4O11Sna C34H25Br5N4O8
MS m/z 424 (23), 423 (11), 422 (48), 421 (6), 420 (24), 398 (24), 397 (10), 396 (13), 3959 (11), 394 (8), 316 (26), 314 (25), 303 (27), 301 (25), 262 (16), 243 (9), 241 (9), 201 (17), 200 (68), 199 (19), 198 (70), 188 (26), 187 (100), 186 (31), 185 (95), 120 (25), 119 (10), 107 (19), 105 (21), 103 (15), 102 (12), 91 (18), 89 (22), 88 (10), 82 (49), 81 (17), 80 (43), 79 (16), 78 (28), 77 (76), 76 (27), 75 (25), 74 (10), 65 (15), 64 (17), 63 (43), 62 (20), 58 (11), 53 (29), 52 (21), 51 (82), 50 (33) No molecular ion; 504 (3), 502 (10), 500 (10), 498 (3), 200 (100), 198 (100), 187 (87), 185 (87) 426 (2), 425 (6), 424 (11), 423 (10), 422 (18), 421 (4), 420 (8), 399 (6), 398 (8), 397 13), 396 (8), 395 (9), 243 (10), 201 (24), 200 (84), 199 (26), 198 (80), 189 (12), 188 (54), 187 (100), 186 (54), 185 (100), 120 (20), 108 (12), 107 (30), 105 (14), 91 (12), 89 (10), 82 (56), 81 (27), 80 (62), 79 (22), 78 (28), 77 (64), 51 (60) MALDI FTMS [M+Na2+] 1062.8130 504 (4), 502 (11), 500 (11), 498 (4), 424 (2), 422 (6), 420 (7), 418 (2), 396 (6), 394 (7), 392 (3), 342 (12), 340 (12), 82 (100), 81 (27), 80 (100), 79 (27) Found: 497.8219, C16H979Br3N2O2 requires 497.8214
MP (°C) NA NA NA NA 250 (dec)
[α]D NA NA NA NA NA
UV λmax (MeOH) nm 220 (4.80) 282 (4.30), 288 sh (3.93) 220 sh (4.70), 280 (3.93), 193 sh (3.87) 220 (4.77), 285 (3.94) 209 (84400), 279 (5550) 210 (4.84), 288 (4.00), 315 (4.00)
IR νmax (KBr) cm−1 NA NA NA (ZnSe film) 3400–3000, 2921, 2852, 1660, 1531, 1486, 1424, 1262, 1234, 1180, 989 (KBr disc) 3600, 2800, 1657, 1633, 1490, 1250
209 Tetramethyl ether (129) 210 (129) 211 (129) 228 (130) 212 (132)
Appearance Colorless prisms White powder Off-white foam Yellow solid White film
Molecular formula C38H35Br5N4O8 C34H26Br6N4O8 C34H26Br4N4O8 C34H25Br4N4O14S2Na2 C34H27Br5N4O9
HR-MS m/z 1073.8310 NA NA MALDI FTMS [M+K3+] 1208.6481 EIMS 504 (7.0), 502 (18.7), 500 (18.7), 498 (5.8), 342 (15.8), 340 (21.1), 199 (7.6), 199 (7.0)
MP (°C) 262–264 NA NA NA NA
[α]D NA NA NA NA NA
UV λmax (MeOH) nm 220 sh, 275 220 sh (4.69), 281 (3.47) 290 (4.18), 315 (4.19) 207 (82300), 321 (12400) 208 (5.1), 280 (3.9)
IR νmax (KBr) cm−1 1670, 1565, 1520, 1495, 1455, 1043 3500–2800, 1665, 1658, 1630, 1500, 1450, 1420, 1280, 1245, 1020, 980 3600–2900, 1663, 1635, 1490, 1455, 1430, 1250, 1015, 1000, 990 (ZnSe film) 3300–2860, 1670, 1653, 1571, 1523, 1482, 1418, 1277, 1240, 1051, 1026, 1005 (Film on NaCl plate) 3340, 1700, 1660, 1590, 1530, 1490, 1450, 1420, 1360, 1280, 1240, 990
212 Tetramethyl ether (132) 213 (132) 213 Tetramethyl ether (132) 214 (132) 215 (132)
Appearance White powder White powder NA Colorless oil Whitish film
Molecular formula C37H33Br5N4O9 C34H28O8N4Br4 NA C34H28O9N4Br4 C34H26O8N4Br4
MS m/z FABMS [p-nitrobenzyl alcohol/magic bullet (dithiothreitol/dithioerythritol) matrix] 1076.9 (33.2), 1074.9 (52.5), 1072.8 (24.7), 1070.8 (19.9). HRFABMS 1110.8194 (C38H35N4O979Br481BrNa requires 1110.8198), 1112.8194 (C38H35N4O979Br381Br2Na requires 1112.8178), 1114.8035 (C38H35N4O979Br281Br3Na requires 1114.8157), 1116.7491 (C38H35N4O979Br81Br4Na requires 1116.8137) FABMS (Magic bullet matrix) 942 (1), 940 (2), 938 (2), 936 (1) [M+] FABMS 1014 (7.1) [M+Na]+, 1016 (21.1), 1018 (28.3), 1020 (26.3), 1022 (1.2). HREIMS 511.8354 (34.4), 513.8460 (95.8), 515.88416 (100), 517.8290 (37.5) NA NA
MP (°C) NA NA NA NA NA
[α]D NA NA NA NA NA
UV λmax (MeOH) nm NA 208 (5.1), 280 (4.0) NA 210 (4.7), 277 (3.7) 208 (4.3), 285 (3.4), 331 (3.5)
IR νmax (KBr) cm−1 NA (Film) 3420–3200, 1710, 1660, 1620, 1585, 1450, 1420, 1360, 1230 NA (Film) 3340 br, 1698, 1662, 1590, 1545, 1483, 1421, 1290, 1240 (Film) 3300 br, 1718, 1662, 1646, 1544, 1495, 1479, 1447, 1418, 1284, 1243
216 Methyl ether (142) 217 (131) 217 Methyl ether (131) 226 (141)
Appearance White amorphous solid White powder White powder NA
Molecular formula C38H35N4O9Br5 C34H28Br4N4O8 C38H36Br4N4O8 C34H27Br4N4O11S
MS m/z 1096 (0.5), 1094 (2.0), 1092 (4.1), 1090 (4.2), 1088 (2.4), 1086 (0.7), 1078 (1.0), 1076 (3.7), 1074 (7.2), 1072 (6.5), 1070 (3.4), 1068 (0.8), 1065 (1.1), 1063 (2.3), 1061 (5.6), 1059 (5.3), 1057 (3.0), 1055 (0.8), 1047 (1.1), 1045 (3.2), 1043 (5.6), 1041 (5.0), 1039 (2.9), 1037 (0.7), 1015 (1.3), 1013 (2.2), 1011 (2.7), 1009 (2.1), 1007 (0.9), 648 (0.4 ), 632 (0.8), 630 (0.6), 602 (3.1), 600 (5.7), 598 (2.8), 592 (1.2), 590 (1.6), 571 (8.0), 569 (13.9), 567 (7.6), 551 (2.0), 549 (5.1), 547 (4.9), 545 (2.3), 536 (2.5), 534 (3.6), 532 (4.6), 530 (3.3), 438 (21.1), 436 (40.4), 434 (20.8), 412 (12.9), 411 (14.1), 410 (19.6), 409 (14.0), 408 (10.0), 342 (20.5), 340 (18.3), 318 (5.6), 316 (13.8), 314 (10.4), 276 (22.5), 261 (8.8), 169 (9.2), 115 (9.4), 82 (41.5), 80 (42.1), 31 (73.6), 29 (100.0). HREIMS 1089.8312. CIMS (Showed one extra Br) [M+Br]+ 1178 (122.7), 1176 (37.3), 1174 (72.2), 1172 (92.9), 1170 (56.4), 1168 (21.8), 1166 (1.2), 1096 (21.0), 1094 (52.0), 1092 (74.2), 1090 (54.0), 1088 (22.6), 1086 (2.4) EI: 520 (4), 518 (4), 516 (3), 396 (9), 394 (16), 392 (8), 342 (23), 340 (24), 317 (8), 316 (7), 315 (10), 57 (100) EI: 1000 (4), 998 (14), 996 (20), 994 (13), 992 (4), 969 (4), 967 (10), 965 (14), 963 (9), 518 (20), 516 (530, 514 (54), 512 (18420 (16), 419 (16), 417 (21), 376 (33), 375 (53), 73 (52), 333 (31), 332 (97), 331 (31), 330 (100) HRFABMS: 1018.8064 [M–Na]−
MP (°C) NA 177–179 107–109 NA
[α]D +2.7° (c 0.77, CH2Cl2) 0.0° (c 1.52, CH2Cl2) NA
UV λmax (MeOH) nm NA 209 (81100), 283 (6200) 209 (76400), 276 (7450) 280 (4800), 204 (74000)
IR νmax (KBr) cm−1 (Film) 3327, 2932, 2857, 1669, 1487 3413, 1666 NA
218 (133) 219 (134) 220 (135) 221 (135)
Appearance NA White amorphous solid NA NA
Molecular formula C38H25Br5N4O8 C34H27N4O8Br5 C34H27Br5N4O8 C34H28Br4N4O9
MS m/z EIMS 424 (2.4), 422 (4.5), 420 (2.5), 316 (3.4), 314 (2.6), 303 (2.7), 301 (3.1) HREIMS 421.9089 HRFABMS 1016.7785 [M+H]+ HRFABMS 1018.7792 [M+H]+ HRFABMS 956.8606 [M+H]+
MP (°C) NA NA NA NA
[α]D NA Negative, too small to be measured NA NA
UV λmax (MeOH) nm 284 (4.3), 292 (4.3), 314 (4.4) NA (Nujol) 280 (3.6) (Nujol) 278 (4.1)
IR νmax (KBr) cm−1 (Nujol) 3500–3300, 1655, 1580, 1530, 1500, 1455, 1425, 1280, 1245, 1230, 1180 NA 3500–3300, 1650, 1630, 1480, 1240, 1225 3600–3100, 1660, 1640, 1490, 1470, 1285, 1220
222 (138) 223 (139) 224 (130) 225 (140) 225 Tetramethyl ether (140)
Appearance Colorless amorphous solid Colorless amorphous powder Colorless solid Amorphous white solid Pale yellow gum
Molecular formula C34H28Br4N4O8 C34H27Br5N4O8 C34H28Br4N4O8 C34H29N4O8Br3 C38H37N4O8Br3
MS m/z FABMS [M++1] 613 (4.9), 581 (1.8), 461 (5.3), 427 (1.5) HRFABMS 940.8705 FABMS 1018.8 MALDI FTMS [M+Na+] 958.8588 ESIMS [M+Na]+ 887 (40), 885 (100), 883 (96), 881 (32) HRESIMS 886.9394, 884.9406, 882.9412, 880.9431 HRESI: 920 (24),
MP (°C) NA NA NA NA NA
[α]D NA NA NA NA NA
UV λmax (MeOH) nm NA NA 209 (84400), 279 (5550) 279 (3.4), 3.83 (2.99) 205 (4.71)
IR νmax (KBr) cm−1 NA NA (ZnSe film) 3400–3000, 2921, 2852, 1660, 1531, 1486, 1424, 1262, 1234, 1180, 989 3422, 2925, 1743, 1654, 1697, 1490, 1380, 1235, 1044 3054, 2970, 2954, 2854, 1735, 1676, 1376,
231 (41) 237 (41) 232:233 3:1 (41) 238 (41)
Appearance Colorless oil Colorless oil Colorless solid
Molecular formula C17H16Br2N2O4 C18H18Br2N2O4 C17H15Br3N2O4 C18H18Br3N2O4
MS m/z EIMS 474 (10), 472 (19), 470 (10), 458 (7), 456 (16), 454 (7), 256 (9), 214 (23), 213 (91), 212 (33), 211 (84), 201 (26), 200 (97), 199 (27), 198 (98), 188 (13), 187 (95), 186 (15), 185 (100), 132 (43), 120 (31), 77 (42). HREIMS 469.9437 (C17H1681Br2N2O4 calcd 473.9430), 471.9445 (C17H1679Br81BrN2O4 calcd 471.9457), 469.9467 (C17H1679Br2N2O4 calcd 473.9477) EIMS 488 (6), 486 (13), 484 (6), 472 (6), 470 (11), 468 (6), 288 (12), 286 (12), 228 (21), 227 (97), 226 (20), 225 (100), 201 (38), 200 (30), 199 (38), 198 (27), 187 (50), 185 (53), 146 (52), 120 (18), 103 (33), 77 (38). HREIMS 487.9615 (C18H1881Br2N2O4 calcd 487.9593), 485.9609 (C18H1879Br81BrN2O4 calcd 485.9614), 483.9633 (C18H1879Br2N2O4 calcd 485.9634) EIMS 554 (4), 552 (14), 550 (14), 548 (5), 293 (33), 291 (67), 289 (34), 267 (24), 265 (50), 263 (24), 213 (41), 212 (51), 211 (24), 198 (76), 187 (91), 185 (100), 132 (28), 120 (25), 77 (49). HREIMS 553.8549 (C17H1581Br3N2O4 calcd 553.8522), 551.8536 (C17H1579Br81Br2N2O4 calcd 551.8542), 549.8562 (C17H1579Br281BrN2O4 calcd 549.8562), 547.8570 (C17H1579Br3N2O4, calcd 547.8582) EIMS 568 (2), 566 (6), 564 (7), 562 (2), 552 (2), 550 (7), 548 (8), 546 (2), 307 (30), 305 (61), 303 (30), 292 (14), 290 (25), 288 (13), 281 (10), 279 (17), 277 (9), 271 (7), 269 (23), 267 (10), 201 (15), 200 (96), 199 (18), 198 (100), 187 (44), 185 (48), 183 (17), 181 (15), 143 (18), 120 (18), 77 (17). HREIMS 567.8672 (C18H1881Br3N2O4 calcd 567.8679), 565.8701 (C18H1879Br81Br2N2O4 calcd 565.8699), 563.8715 (C18H1879Br281BrN2O4 calcd 563.8719), 561.8716 (C18H1879Br3N2O4 calcd 561.8739)
UV λmax (MeOH) nm 210 (4.53), 281 (3.88) 213 (4.53), 280 (3.87) NA 213 (4.50), 281 (3.87)
IR νmax (KBr) cm−1 (NaCl film) 3383, 3000, 1659, 1537, 1495, 1422, 1283, 1256 (NaCl film) 3385, 3283, 1657, 1537, 1497, 1283, 1256 (NaCl film) 3393, 1657, 1476 (NaCl film) 3300, 1661, 1537, 1497, 1472, 1422, 1260, 993
234 (41) 234a (41) 235 (41) 235a:236a (41)
Appearance Colorless solid Colorless solid Mixture with hemibastadinol-3 Colorless solid
Molecular formula C17H17Br2NO4 C19H21Br2NO4 C17H16Br3NO4 C19H20Br3NO4
MS m/z EIMS 461 (>1), 459 (0.3), 457 (>1), 443 (6), 441 (13), 439 (6), 244 (30), 242 (35), 241 (18), 227 (14), 225 (15), 201 (19), 200 (98), 199 (21), 198 (100), 187 (28), 185 (28), 120 (20), 107 (23), 77 (18) HREIMS 460.9477 (C17H1781Br2NO4 calcd 460.9494), 458.9483 (C17H1779Br81BrNO4 calcd 458.9514), 456.9507 (C17H1779Br2NO4 calcd 456.9534) HRFABMS [M+H] 485.9897 (C19H2279Br2NO4, calcd 485.9915) EIMS 541 (<1), 539 (< 1), 537 (<1), 535 (<1), [M+–H2O] 523 (2), 521 (7), 519 (6), 517 (2), 244 (9), 242 (10), 201 (15), 200 (100), 199 (16), 198 (100), 187 (16), 185 (17), 120 (20), 77 (13). HREIMS 540.8558 (C17H1681Br3NO4 calcd 540.8572), 538.8586 (C17H1679Br81Br2NO4 calcd 538.8593), 536.8631 (C17H1679Br281BrNO4 calcd 536.8612), 534.8605 (C17H1679Br3NO4 calcd 534.8633), [M+–H2O] 522.8446 (C17H1481Br3NO3 calcd 522.8464), 518.8497 (C17H1479Br281BrNO3 calcd 518.8504), 516.8509 (C17H1479Br3NO3 calcd 516.8524) HRFABMS [M+H], 563.9019 (C19H2079Br3NO4, calcd 563.9020)
MP (°C) NA NA NA NA
[α]D −31° (c 1.83, MeOH) −23° (c 0.66, MeOH) −24° (c 0.10, MeOH) NA
UV λmax (MeOH) nm 208 (4.43), 281 (3.69) 208 (4.45), 281 (3.60) NA NA
IR νmax (KBr) cm−1 (Film) 3381, 1643, 1541, 1495, 1420, 1289 (Film) 3387, 1651, 1497, 1279, 1256, 1057 (Film) 3381, 1643, 1539, 1478, 1279 3393, 2930, 1651, 1537, 1497, 1472, 1258
236 (41) 239 (145) 240 (145) 241 (145)
Appearance Mixture with hemibastadinol-2 White needles Colorless gum White needles
Molecular formula C17H16Br3NO4 C19H17Br2NO4 C19H17Br2NO4 C19H18BrNO4
MS m/z EIMS 541 (<1), 539 (<1), 537 (<1), 535 (<1), [M+–H2O] 523 (2), 521 (7), 519 (6), 517 (2), 244 (9), 242 (10), 201 (15), 200 (100), 199 (16), 198 (100), 187 (16), 185 (17), 120 (20), 77 (13) HREIMS 540.8558 (C17H1681Br3NO4 calcd 540.8572), 538.8586 (C17H1679Br81Br2NO4 calcd 538.8593), 536.8631 (C17H1679Br281BrNO4 calcd 536.8612), 534.8605 (C17H1679Br3NO4 calcd 534.8633), [M+–H2O] 522.8446 (C17H1481Br3NO3 calcd 522.8464), 518.8497 (C17H1479Br281BrNO3 calcd 518.8504), 516.8509 (C17H1479Br3NO3 calcd 516.8524) EIMS 484.9 (3), 482.9 (6), 480.9 (3), 177 (17), 149 (20), 134 (100), 106 (25), 78 (15), 77 (13) HREIMS 480.9526 EIMS 484.9 (4), 482.9 (8), 480.9 (4), 177 (21), 149 (21), 134 (100), 106 (19), 78 (10), 77 (9) HREIMS 480.9526 EIMS 405 (7), 403 (6), 229 (7), 227 (7), 177 (11), 149 (16), 78 (13), 77 (15) HREIMS 403.418
MP (°C) NA 169–171 NA 173–175
[α]D −24° (c 0.10, MeOH) NA NA NA
UV λmax (MeOH) nm NA (EtOH) 205 (10900), 220 (10300), 225 sh (9900), 325 (15900) (EtOH) 206 (10800), 214 (9600), 230 sh (9400), 328 (14100) (EtOH) 204 (13200), 227 sh (10600), 329 (14100)
IR νmax (KBr) cm−1 (NaCl film) 3381, 1643, 1539, 1478, 1279 (CHCl3) 3410, 3018, 2927, 2855, 1735, 1650, 1607, 1513, 1496, 1468, 1423, 1265, 1171, 1087, 909 (CHCl3) 3409, 3018, 1700, 1650, 1607, 1513, 1468, 1423, 1250, 1171, 1087, 1001, 949 (CHCl3) 3409, 3018, 2927, 2855, 1730, 1693, 1653, 1607, 1513, 1486, 1463, 1441, 1259, 1171, 1089, 1054, 1019
242 (145) 243 (146) 244 (146) 245 (146) 247 (123)
Appearance Colorless gum NA NA NA Yellow amorphous solid
Molecular formula C19H18BrNO4 C24H28Br2N2O4 C24H28BrIN2O4 C24H28I2N2O4 C17H25Br2N3O2
MS m/z EIMS 405 (8), 403 (7), 229 (8), 227 (7), 177 (12), 149 (18), 135 (9), 134 (100), 106 (21), 78 (13), 77 (16) HREIMS 403.0418 FABMS 571, 569, 567 [M+H]+ FABMS 617, 615 [M+H]+ FABMS 663 [M+H]+ FABMS 803, 805, 807, 809, 811 [M]+, 466, 468, 470, 426, 428, 430, 409, 411, 413 HRFABMS 806.9007 [M]+
MP (°C) NA NA NA NA NA
[α]D NA NA NA NA NA
UV λmax (MeOH) nm (EtOH) 203 (11100), 224 sh (9100), 326 (11700) NA NA NA 214 (20600), 258 sh (3800)
IR νmax (KBr) cm−1 (CHCl3) 3413, 3018, 2935, 1710, 1650, 1607, 1513, 1466, 1425, 1248, 1168, 1087, 1001, 949 (Neat) 3286, 1635, 1542, 1515, 1455, 1256 (Neat) 3283, 1628, 1537, 1514, 1443, 1260 (Neat) 3276, 1629, 1538, 1514, 1435, 1256 NA
246 (38) 248 (150) 249 (151) 250 (151) 251 (152) 252 (152)
Appearance Amorphous solid NA Small yellow crystals Small yellow crystals Yellow amorphous solid Yellow amorphous solid
Molecular formula C15H17N4O2Br2 C14H10O11S2Br2 C17H16Br2N4O2 C16H14Br2N4O2 C23H24N3O3Br3 C22H22N3O3Br3
MS m/z FABMS 443, 445, 447 NA HREIMS 467.9624 [M+] HREIMS 453.9460 [M+] FABMS 628, 630, 632, 634 (1:3:3:1) [M+H]+ HRFABMS 631.9403 [M+H]+ (Δ −0.2 mmu) FABMS 614, 616, 618, 620 (1:3:3:1) [M+H]+ HRFABMS 615.9280 (M+H)+ (Δ +1.8 mmu)
MP (°C) NA NA 236 242 NA NA
[α]D NA NA NA NA NA NA
UV λmax (MeOH) nm (EtOH) 226 (12200), 298 (32000) NA NA NA 285 (4000), 350 (1000) 285 (5000), 350 (1200)
IR νmax (KBr) cm−1 (Dry film) 1690 (Film) 3454 (br d), 1631, 1257 (br d), 1059, 1018 NA NA 3422, 1680 3422, 1680
253 (153) 254 (153) 255 (153) 256 (154) 257 (154)
Appearance Needles White amorphous solid White amorphous solid White solid White gum
Molecular formula C18H15N2O3Br C18H15N2O3I C18H16N2O3 C19H21N2O2Br C19H20N2O2Br2
MS m/z HRFABMS [M++H] 387.0313 HREIMS 434.0146 HREIMS 308.1159 HREIMS 370.0681 [M–H2O]+ HREIMS 465.9891 [M+]
MP (°C) 178–179 NA NA NA NA
[α]D NA NA NA NA NA
UV λmax (MeOH) nm (MeOH) 324 (8400), 290 (5000), 274 (9600), 267 (9900), 255 (10300), 205 (41400) (MeOH+NaOH), 309 (9800), 272 (8600), 266 (9900), 247 (1600), 207 (58500) (MeOH) 325 (6600), 274 (8200), 267 (sh), 254 (9100), 230 (sh), 205 (50000) (MeOH+NaOH), 311 (8200), 274 (7600), 267 (sh), 247 (13200), 203 (79100) (MeOH) 324 (4600), 285 (sh), 272 (5700), 266 (6100), 254 (6400), 205 (19200) (MeOH+NaOH), 218 (4600), 272 (5300), 266 (6100), 246 (8300), 205 (21400) 288 (sh), 280 (6400), 221 (30600), 208 (29000) (DMSO) 299 (sh), 287 (2500), 279 (sh), 221 (30600), 208 (29000)
IR νmax (KBr) cm−1 (CHCl3) 3010, 1680, 1635, 1500, 1420, 1215, 1120 (neat NaCl) 2930, 1680, 1640, 1505, 1420 NA (CHCl3) 3470, 3330 br, 1605, 1500, 1460, 1445, 1420, 1285, 1260, 1055 (CHCl3) 3470, 3330 br, 1605, 1500, 1460, 1445, 1420, 1285, 1260, 1055
258 (155) 259 (164) 260 (158) 261 (158) 262 (159)
Appearance Gum NA Colorless prisms Colorless crystals Colorless glass
Molecular formula C12H17NO5 C36H45IN4O6Br C28H40IN3O6 C28H40BrN3O6 C28H40N3O6Cl
MS m/z FABMS 256 (M+H+, 100) HRFABMS 256.11858, 256.11850 NA FABMS 642 (100) [MH+], 516 (50), 393 (15), 276 (30), 217 (50), 150 (50) FABMS 594 (95) [MH+], 516 (60), 345 (30), 267 (30), 228 (80), 150 (100) HREIMS 549.2603, 551.2562 (Δ −0.2, −1.4 mmu)
MP (°C) NA NA 217–218 203–204 NA
[α]D +25.51° (c 0.002, MeOH) +35° (c 3.62, CHCl3) +53° (c 0.04, CHCl3) +101° (c 0.04, CHCl3) NA
UV λmax (MeOH) nm NA 281 (5400), 290 (4100) 219 (13800), 284 (3200), 292 (3000) 214 (15400), 281 (2700), 290 (2500) NA
IR νmax (KBr) cm−1 NA (CDCl3) 3400–3100, 1710, 1660, 1630 (CHCl3) 1725, 1670, 1655, 1630 (CHCl3) 3510, 3410, 1725, 1670, 1655 (sh), 1630 NA
263 (159) 264 (159) 265 (159) 266 (164) 267 (161)
Appearance Colorless glass NA NA Colorless glass NA
Molecular formula C27H38N3O6I C27H38N3O6Br C27H38N3O6Cl C28H38N3O7I C34H44O7N3I
MS m/z HREIMS 627.1798 (Δ −0.9 mmu) HREIMS 579.1955, 581.1909 (Δ +1.1, −1.6 mmu) HREIMS 535.2449, 537.2442 (Δ 0.0, +2.2 mmu) HREIMS 655.1760 (ΔM, 0.6 mmu) EIMS 773 (48) [M]+, 706 (10), 608 (15), 552 (5), 460 (54), 413 (17), 321 (24), 276 (100), 250 (19), 162 (73), 109 (46), HREIMS 733.2199
MP (°C) NA NA NA NA 186–189
[α]D NA NA NA NA +19.1° (c 0.17, CHCl3)
UV λmax (MeOH) nm NA NA NA NA 215 (12500), 280 (2800)
IR νmax (KBr) cm−1 NA NA NA 3313, 1732, 1675, 1635 3495, 1724, 1670
268 (161) 271 (164) 272 (164) 273 (164) 274 (164)
Appearance NA Colorless glass Colorless glass Colorless glass Colorless glass
Molecular formula C34H44O7N3Br C28H39N3O7Br C28H39N3O7Cl C28H40N3O7I C28H39N3O7Br
MS m/z EIMS 685 (38) [M]+, 657 (10), 460 (52), 413 (24), 273 (26), 228 (100), 162 (87), 109 (59) HREIMS 685.2374 HRDCIMS 610.19509, 608.19713 (C28H39N3O781Br, C28H39N3O779Br); found 610.19431, 608.19508 (Δ −1.49, −3.38 ppm) HRDCIMS 565.23688, 563.23981 (C28H39N3O737Cl, C28H39N3O735Cl); found 565.23956, 563.24011 (Δ −4.7, −0.5 ppm) HREIMS 658.19892, found 658.19767 (Δ −1.91 ppm) HREIMS 611.20294, 609.20496 (C28H40N3O781Br, C28H40N3O779Br); found 611.20371, 609.20519 (Δ −1.3, −0.4 ppm)
MP (°C) 168–170 NA NA NA NA
[α]D +39.3° (c 0.17, CHCl3) NA NA NA NA
UV λmax (MeOH) nm 214 (14000), 280 (3000) NA NA NA NA
IR νmax (KBr) cm−1 (CHCl3) 3500, 1725, 1670 NA NA NA NA
275 (164) 276 (164) 277 (164) 278 (164)
Appearance Colorless glass Colorless glass Colorless glass Colorless glass
Molecular formula C28H39N3O7Cl C28H40O7N3I C28H39N3O7Br C27H38O7N3I
MS m/z HREIMS 567.25250, 265.25549 (C28H40N3O737Cl, C28H40N3O7735Cl); found 567.25184, 565.25403 (Δ 1.2, 2.6 ppm) HREIMS 658.19892, found 658.19880 (Δ −0.19 ppm) HREIMS 611.20294, 609.20496 (C28H40N3O781Br, C28H40N3O7779Br); found 611.20374, 609.20515 (Δ −1.3, −0.3 ppm) HREIMS 643.17548, found 643.17539 (Δ 0.1 ppm)
MP (°C) NA NA NA NA
[α]D NA NA NA NA
UV λmax (MeOH) nm NA NA NA NA
IR νmax (KBr) cm−1 NA NA NA NA
269(164) 270 (164) 280 (167) 281 (168) 282 (167)
Appearance Colorless glass Colorless amorphous solid Yellowish needles Yellow oil Yellowish, fluorescent oil
Molecular formula C30H44N3O6I C38H21Br8NO7 · (CH3)2CO C30H13Br8NO6 C24H15Br4NO5
MS m/z HRMS 670.2335 [MH+] FABMS 656 [M+H]+ NA EIMS 1123 (20) [M+], 596 (55), 526 (55), 448 (15), 337 (20), 279 (55) HRMS 719.0348
MP (°C) NA NA 285 NA NA
[α]D +30° (c 0.027, CHCl3) +5.2° NA NA NA
UV λmax (MeOH) nm NA 219 (13270), 284 (4000), 292 (3000) 36 (17000), 300s (11700) NA 400 (2000), 280 (5250) (MeOH/KOH) 515 (2800), 400 (2800), 300 (5000)
IR νmax (KBr) cm−1 (Neat) 3420, 1720, 1670, 1655, 1630 NA (CHCl3) 3500, 2900, 1645, 1580, 1514, 1300 (Neat) 3500, 1645, 1582, 1515 3500, 2919, 1699, 1400
283 (167) 284 (168) 229 (41) 230 (41)
Appearance Yellowish fluorescent oil Yellow oil White solid White solid
Molecular formula C25H17Br4NO5 C16H6Br4O5 C20H22Br2N2O4 C20H21Br3N2O4
MS m/z HRMS 732.0619 [M+H]+ HREIMS 597.6915 EIMS 516 (1), 514 (2), 512 (1), 258 (2), 257 (2), 256 (3), 255 (9), 228 (10), 227 (64), 226 (14), 225 (65), 215 (10), 214 (38), 213 (11), 212 (46), 201 (61), 199 (65), 149 (48), 146 (40), 57 (100) HREIMS 511.9948 EIMS 596 (0.4), 594 (2), 592 (2), 590 (0.4), 565 (<<1) 563 (1), 561 (1), 559 (<<1) 366 (0.3), 364 (1), 362 (0.4), 338 (0.6), 336 (2), 334 (0.7), 308 (1), 307 (10), 306 (4), 305 (20), 304 (4), 303 (10), 302 (1), 292 (5), 290 (10), 288 (5), 281 (6), 279 (14), 277 (7), 257 (2), 255 (2), 224 (2), 223 (3), 222 (3), 221 (2), 215 (15), 214 (97), 213 (16), 212 (100), 201 (30), 199 (34), 185 (4), 183 (11), 181 (8), 134 (16), 105 (17), 77 (39) HREIMS 589.9049
MP (°C) NA NA NA NA
[α]D NA NA NA NA
(MeOH) nm NA NA
(KBr) cm"1 3500, 1702, 1698, 1400 (Neat) 3460, 1761, 1721, 1475 NA NA