Table 1. NMR Spectral Data for 1 in DMSO-d6 Acquired with a 700 MHz Instrumenta.
| position | δC | δH(mult,J,Hz) | COSY | HMBC | ROESY |
|---|---|---|---|---|---|
| 1 | 13.9 (CH) | 0.69 dd (9.6, 2.2) | H-2a, H-2b | C-3, C-5, C-6, C-7, C-10, C-11, C-12 | H-2b, H-19, 6′-OH |
| 2a | 29.8 (CH2) | 0.85 m | H-1 | C-1, C-11 | H-12 |
| 2b | 2.16 ddd (15.2, 9.6, 2.2) | H-1, H-4b | C-1, C-3, C-4, C-11 | H-1, H-2a, H-20, H-1′, H-5′, 6′-OH | |
| 3 | 72.5 (C) | ||||
| 4a | 33.9 (CH2) | 0.77 m | H-5a, H-5b | C-2, C-5, C-20, C-1′ | H-12 |
| 4b | 1.35 m | H-2b, H-5b | C-2, C-3, C-5, C-6 | H-5b, H-20, H-1′ | |
| 5a | 21.3 (CH2) | 1.15 m | H-4a | C-1, C-3, C-4, C-6, C-11 | H-4b, H-5b, H-12 |
| 5b | 1.96 ddd (13.8, 12.4, 7.5) | H-4a, H4b | C-3, C-4, C-6, C-7 | H-4a, H-4b, H-5a, H-19, H-1′, H-2′ | |
| 6 | 24.2 (C) | ||||
| 7 | 35.0 (CH) | 1.35 m | H-8a, H-19 | C-1, C-8, C-9, C-19 | H-9a |
| 8a | 26.8 (CH2) | 0.75 m | H-7, H-9a | C-6, C-7, C-9, C-10, C-19 | H-9b |
| 8b | 1.16 m | H-9b | C-10 | H-9b | |
| 9a | 39.2 (CH2) | 0.91 m | H-8a | C-7, C-10, C-18 | H-7 |
| 9b | 1.47 m | H-8b | C-7, C-8, C-10, C-11, C-18 | H-8a, H-8b, H-18 | |
| 10 | 41.6 (C) | ||||
| 11 | 36.2 (C) | ||||
| 12 | 25.1 (CH2) | 1.27 m | H-13a, H-13b | C-1, C-6, C-10, C-11, C-13, C-14 | H-2a, H-4a, H-13b, H-18 |
| 13a | 27.9 (CH2) | 1.19 m | H-12 | C-12, C-14 | H-13b, H-18 |
| 13b | 1.73 m | H-12, H-14 | C-10, C-11, C-12, C-14, C-15, C-18 | H-12, H-13a, H-14, H-17 | |
| 14 | 61.4 (CH) | 1.19 m | H-13b, H-15 | C-10, C-13, C-15, C-18 | H-13b |
| 15 | 28.5 (CH) | 1.56 o (6.7) | H-14, H-16, H-17 | C-10, C-13, C-14, C-16, C-17 | H-16, H-17, H-18 |
| 16 | 23.3 (CH3) | 0.91 d (6.6) | H-15 | C-10, C-14, C-15, C-17 | H-15, H-18 |
| 17 | 23.0 (CH3) | 0.87 d (6.6) | H-15 | C-14, C-15, C-16 | H-13b, H-15 |
| 18 | 19.0 (CH3) | 0.64 s | C-1, C-9, C-10, C11, C-14 | H-9b, H-12, H-13a, H-15, H-16 | |
| 19 | 19.1 (CH3) | 1.02 d (6.4) | H-7 | C-6, C-7, C-8 | H-1, H-5b, H-2′, H-4′ |
| 20 | 25.8 (CH3) | 1.00 s | C-1, C-2, C-3, C-4, C-5 | H-2b, H-4b, H-1′ | |
| 1′ | 94.7 (CH) | 4.39 d (7.7) | H-2′ | C-3, C-2′, C-3′, C-5′ | H-2b, H-4b, H-5b, H-20, H-3′, H-5′ |
| 2′ | 79.3 (CH) | 3.65 dd (8.8, 7.7) | H-1′, H-3′ | C-1′, C-3′ | H-19, H-5b, 3′-OH |
| 3′ | 76.7 (CH) | 3.44 t (8.8) | H-2′, H-4′ | C-1′, C-2′, C-4′, C-5′ | H-1′, 3′-OH, 4′-OH |
| 4′ | 70.7 (CH) | 3.00 td (9.3, 5.3) | H-3′, H-5′ | C-3′, C-5′, C-6′ | H-19, 3′-OH, 4′-OH, 6′-OH |
| 5′ | 76.1 (CH) | 3.13 ddd (9.5, 6.8, 2.3) | H-4′, H-6′a, H6′b | C-1′, C-3′, C-4′, C-6′ | H-2b, H-1′, 4′-OH |
| 6′a | 61.8 (CH2) | 3.37 m | H-5′ | C-4′, C-5′ | H-6′b |
| 6′b | 3.72 ddd (11.2, 4.7, 2.3) | H-5′ | C-4′, C-5′ | H-6′a, 4′-OH, 6′-OH | |
| 3′-OH | 5.63 s | C-2′, C-3′, C-4′ | H-2′, H-3′, H-4′ | ||
| 4′-OH | 4.97 d (5.4) | C-3′, C-4′, C-5′ | H-3′, H-4′, H-5′, H-6′b | ||
| 6′-OH | 4.22 t (5.2) | C-5′, C-6′ | H-1, H-2b, H-4′ |
a
δC, δH—experimental carbon and proton chemical shifts, mult—multiplicity, J—coupling constant, s—singlet, d—doublet, m—multiplet, t—triplet, o—octet.