Table 3.
NMR Data for Argutins F-H (6 -8) (600 MHz, CDCl3)
| argutin F (6) | argutin G (7) | argutin H (8) | ||||
|---|---|---|---|---|---|---|
| |
||||||
| position | δC, mult | δH mult (J, Hz) | δC, multa | δH mult (J, Hz) | δC, multa | δH mult (J, Hz) |
| 1a | 27.5, CH2 | 2.00, m | 27.5 | 2.04, m | 29.5 | 2.09, m |
| 1b | 1.89, m | 1.95,b m | 2.01,c m | |||
| 2 | 66.4, CH | 5.46, br t (4.0) | 65.5 | 5.49,b m (3.7) | 63.6 | 4.45, m (4.0) |
| 3 | 122.2, CH | 5.97, br d (4.0) | 122.3 | 6.02, br d (3.7) | 127.0 | 5.99, br d (4.0) |
| 4 | 145.3, C | — | 146.8 | — | 141.9 | — |
| 5 | 54.0, C | — | 52.8 | — | 53.2 | — |
| 6 | 73.8, CH | 3.72, dd (10.8, 4.3) | 77.0 | 3.54, d (9.7) | 76.3 | 5.06, d (10.2) |
| 7a | 38.1, CH2 | 1.70,b m | 73.2, CH | 3.68, dd (10.2, 9.7) | 71.7, CH | 3.76, dd (10.7, 10.2) |
| 7b | 1.65, m | — | — | |||
| 8 | 36.6, CH | 1.70,b m (6.2) | 42.2 | 1.65, m (10.2, 6.9) | 43.0 | 1.76,b m (10.7, 7.0) |
| 9 | 38.6, C | — | 39.0 | — | 39.4 | — |
| 10 | 42.6, CH | 1.92, dd (13.6, 5.0) | 41.8 | 1.94,b m | 40.8 | 2.01,c m |
| 11a | 38.9, CH2 | 1.78, dd (15.6, 6.8) | 39.7 | 1.80, m | 39.3 | 1.78,b m |
| 11b | 1.22, m (15.6) | 1.27,b | 1.25,b m | |||
| 12 | 83.4, CH | 4.73, dd (6.8, 2.4) | 82.8 | 4.80, dd (6.6, 2.4) | 82.7 | 4.80, dd (7.3, 2.1) |
| 13 | 146.2, C | — | 146.2 | — | 146.1 | — |
| 14 | 135.6, CH | 6.27, dd (17.7, 11.3) | 135.6 | 6.27, dd (17.6, 11.2) | 135.5 | 6.27, dd (17.7, 11.3) |
| 15a | 116.7, CH2 | 5.46, d (17.7) | 116.3 | 5.47,b (17.6) | 116.6 | 5.47, d (17.7) |
| 15b | 5.15, d (11.3) | 5.13, dd (11.2) | 5.14, d (11.3) | |||
| 16a | 117.5, CH2 | 5.26, s | 117.3 | 5.24, s | 117.1 | 5.27, s |
| 16b | 5.16, s | 5.16, s | 5.17, s | |||
| 17 | 16.2, CH3 | 1.06, d (6.2) | 10.7 | 1.20, d (6.9) | 10.7 | 1.20, d (7.0) |
| 18 | 96.0, CH | 6.72, t (1.4) | 95.4 | 6.75, br s | 95.0 | 6.40, br t (1.6) |
| 19 | 98.1, CH | 6.41, br s | 97.9 | 6.44, br s | 98.0 | 6.45, br s |
| 20 | 24.2, CH3 | 1.02, s | 24.6 | 1.04, s | 24.8 | 1.14, s |
| 1′ | 166.2, C | — | 166.1 | — | 166.5 | — |
| 2′ | 115.7, CH | 5.59, d (11.3) | 115.4 | 5.60, d (11.3) | 114.2 | 5.64, d (11.3) |
| 3′ | 146.8, CH | 6.55, t (11.3) | 146.7 | 6.59, t (11.3) | 148.4 | 6.63, t (11.3) |
| 4′ | 127.4, CH | 7.36, dd (15.3, 11.3) | 127.2 | 7.37, dd (15.2, 11.3) | 127.1 | 7.32, dd (15.2, 11.3) |
| 5′ | 147.0, CH | 6.09, ddd (15.3, 7.7, 7.2) | 147.3 | 6.11, ddd (15.3, 7.6, 7.3) | 147.4 | 6.10, ddd (15.2, 7.6, 7.2) |
| 6′ | 33.6, CH2 | 2.18, ddd (14.3, 7.2, 7.0) | 33.3 | 2.19, ddd (14.4, 7.3, 7.1) | 33.5 | 2.15, ddd (14.4, 7.2, 7.0) |
| 7′ | 29.0, CH2 | 1.41, ddd (14.7, 7.4, 7.0) | 28.6 | 1.42, ddd (14.7, 7.4, 7.1) | 28.8 | 1.40, ddd (14.6, 7.4, 7.0) |
| 8′ | 31.9, CH2 | 1.26,b m | 31.7 | 1.28,b m | 31.9 | 1.25,b m |
| 9′ | 22.9, CH2 | 1.28,b m (6.8) | 22.6 | 1.29,b m (6.7) | 23.0 | 1.27,b m (6.9) |
| 10′ | 14.7, CH3 | 0.86, t (6.8) | 14.0 | 0.87, t (6.7) | 13.8 | 0.85, t (6.9) |
| 18-OAc | 171.1, C | — | 170.8 | — | 170.5 | — |
| 21.6, CH3 | 2.06, s | 21.4 | 2.08, s | 21.2 | 2.02, s | |
| 19-OAc | 169.9, C | — | 170.0 | — | 169.8 | — |
| 22.2, CH3 | 1.97, s | 21.7 | 1.97, s | 21.8 | 1.94, s | |
a
Carbon multiplicities are identical to those of argutin F unless specifically noted.
b
0 Signals overlapped.
c
Signal obscured by overlapping methyl signal.