Table 1. 1H and 13C NMR Chemical Shifts (δ) of Compounds 1–4a.
| 1 | 2 | 3 | 4 | |||||
|---|---|---|---|---|---|---|---|---|
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| position | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC |
| 1a | 1.50, overlap | 32.1 | 1.48, overlap | 32.0 | 1.67, overlap | 29.9 | 1.49, overlap | 33.8 |
| 1b | 1.50, overlap | 1.48, overlap | 1.51, overlap | 1.49, overlap | ||||
| 2a | 1.56, overlap | 18.9 | 1.54, overlap | 18.8 | 1.66, overlap | 23.8 | 1.61, m | 18.9 |
| 2b | 1.48, overlap | 1.47, overlap | 1.66, overlap | 1.49, m | ||||
| 3a | 1.33, overlap | 42.0 | 1.32, overlap | 41.9 | 4.44, dd (10.8, 4.0) | 81.0 | 1.30, m | 43.9 |
| 3b | 1.14, td (12.9, 3.7) | 1.13, td (12.9, 3.4) | 1.15, td (13.3, 3.2) | |||||
| 4 | 33.6 | 33.5 | 37.9 | 34.2 | ||||
| 5 | 1.40, m | 46.6 | 1.40, m | 46.6 | 1.55, m | 45.8 | 1.63, d (1.8) | 47.7 |
| 6a | 1.52, overlap | 21.9 | 1.51, overlap | 21.8 | 1.51, overlap | 21.3 | 5.37, q-like (2.4) | 70.4 |
| 6b | 1.29, overlap | 1.28, overlap | 1.28, overlap | |||||
| 7a | 1.48, overlap | 31.5 | 1.48, overlap | 31.5 | 1.48, overlap | 31.2 | 1.60, overlap | 36.3 |
| 7b | 1.28, overlap | 1.27, overlap | 1.32, overlap | 1.55, overlap | ||||
| 8 | 1.80, m | 36.8 | 1.78, m | 36.8 | 1.76, m | 36.8 | 2.12, m | 31.9 |
| 9 | 77.3 | 77.2 | 77.2 | 77.2 | ||||
| 10 | 43.5 | 43.4 | 43.0 | 43.9 | ||||
| 11a | 1.92, ddd (14.4, 11.7, 6.3) | 36.0 | 1.89, ddd (14.4, 11.8, 6.2) | 35.9 | 1.90, ddd (14.6, 9.9, 7.7) | 35.8 | 1.92, ddd (14.4, 11.9, 6.1) | 35.8 |
| 11b | 1.69, ddd (14.4, 11.3, 5.9) | 1.67, ddd (14.4, 11.5, 5.9) | 1.69, overlap | 1.79, ddd (14.4, 11.5, 5.6) | ||||
| 12 | 2.66, m | 23.5 | 2.61, m | 23.8 | 2.62, m | 23.8 | 2.65, m | 23.7 |
| 13 | 138.1 | 138.3 | 138.1 | 138.0 | ||||
| 14 | 6.11, t (2.8) | 110.2 | 6.00, d (2.6) | 109.4 | 6.00, d (2.6) | 109.6 | 6.03, d (2.6) | 109.4 |
| 15 | 6.82, t (2.8) | 123.5 | 6.70, d (2.6) | 126.5 | 6.71, d (2.6) | 126.7 | 6.83, d (2.6) | 127.5 |
| 16 | 99.3 | 102.0 | 102.1 | 102.1 | ||||
| 17 | 0.94, d (6.6) | 16.6 | 0.93, d (6.8) | 16.6 | 0.94, d (6.8) | 16.4 | 0.96, d (6.8) | 16.3 |
| 18 | 0.86, s | 34.0 | 0.85, s | 33.9 | 0.85, s | 28.5 | 0.94, s | 33.8 |
| 19 | 0.82, s | 22.2 | 0.81, s | 22.2 | 0.84, s | 16.7 | 0.98, s | 23.9 |
| 20 | 0.93, s | 16.4 | 0.92, s | 16.4 | 0.93, s | 16.3 | 1.24, s | 19.3 |
| CN | 114.6 | 114.0 | 114.0 | 114.1 | ||||
| 1′ | 4.01, t (6.9) | 48.0 | 4.04, t (7.0) | 47.9 | 4.11, t (5.2) | 51.3 | ||
| 2′ | 2.09, quintet (6.9) | 26.4 | 2.10, m | 26.2 | 3.91, t (5.2) | 62.3 | ||
| 3′ | 2.26, t (6.9) | 30.9 | 2.30, m | 30.3 | ||||
| 4′ | 172.6 | 176.0 | ||||||
| 5′ | 4.12, q (7.1) | 60.9 | ||||||
| 6′ | 1.24, t (7.1) | 14.4 | ||||||
| OAc-3 | 171.4 | |||||||
| 2.03, s | 21.6 | |||||||
| OAc-6 | 170.8 | |||||||
| 2.03, s | 22.2 | |||||||
| NH | 8.74, br s | |||||||
a
1H NMR measured at 400 MHz, 13C NMR measured at 100 MHz, and spectra obtained in CDCl3 with TMS as internal standard. Assignments were supported with HSQC and HMBC NMR spectra.