Table 1.
1H and 13C NMR spectral data (δ) for compounds 1−3.a
| No. |
1 |
2 |
3b |
|||
| δH | δC | δH | δC | δH | δC | |
| 1a | 35.9 | 61.4 | 1.51 m | 41.8 | ||
| 1b | 1.30 ddd (10.5, 6.0, 4.5) | |||||
| 2a | 2.41 d (16.8) | 47.3 | 56.3 | 1.61 m | 23.2 | |
| 2b | 1.97 d (16.8) | |||||
| 3a | 197.9 | 1.38 dd (12.0, 6.0) | 38.8 | 2.32 ddd (13.2, 3.0, 1.8) | 36.7 | |
| 3b | 1.12 m | 1.98 ddd (13.2, 7.2, 6.0) | ||||
| 4a | 5.80 s | 124.8 | 1.48 m | 27.6 | 149.9 | |
| 4b | 1.37 m | |||||
| 5a | 162.0 | 1.64 ddd (12.0, 6.0, 3.6) | 40.0 | 1.91 dd (12.6, 1.2) | 52.0 | |
| 5b | 1.34 dd (12.0, 6.0) | |||||
| 6a | 2.67 d (9.6) | 55.2 | 57.9 | 2.76 ddd (13.2, 12.6, 1.2) | 26.3 | |
| 6b | 2.66 dd (13.2, 3.0) | |||||
| 7 | 5.61 dd (15.6, 9.6) | 126.5 | 2.19 d (4.8) | 50.3 | 162.3 | |
| 8 | 6.23 d (15.6) | 137.2 | 170.6 | 105.3 | ||
| 9a | 135.9 | 6.08 d (0.6) | 123.8 | 2.27 d (13.2) | 51.7 | |
| 9b | 1.49 d (13.2) | |||||
| 10 | 5.60 dd (7.2, 6.6) | 127.3 | 208.3 | 37.4 | ||
| 11a | 4.32 dd (12.6, 6.6) | 64.4 | 2.03 dd (12.0, 4.8) | 47.9 | 123.1 | |
| 11b | 4.19 dd (12.6, 7.2) | 1.82 d (12.0) | ||||
| 12 | 1.73 s | 12.6 | 0.98 s | 17.9 | 171.9 | |
| 13 | 1.84 s | 23.0 | 0.96 s | 23.0 | 1.78 d (0.6) | 8.2 |
| 14 | 0.95 s | 27.4 | 1.15 s | 28.3 | 1.00 s | 17.3 |
| 15a | 0.88 s | 26.8 | 4.42 dd (17.4, 1.8) | 72.2 | 4.81 d (1.2) | 107.0 |
| 15b | 4.33 dd (17.4, 1.8) | 4.63 d (1.2) | ||||
| 1ʹ | 4.13 d (7.8) | 101.8 | 4.26 d (7.8) | 104.5 | 4.15 d (7.8) | 97.3 |
| 2ʹ | 2.95 t (7.8) | 73.3 | 3.29 t (7.8) | 78.0 | 3.23 ddd (9.0, 7.8, 3.0) | 74.3 |
| 3ʹ | 3.23 dd (9.0, 7.8) | 76.6 | 3.19 t (7.8) | 75.0 | 3.36 t (9.0) | 77.9 |
| 4ʹ | 2.97 t (9.0) | 70.3 | 3.24 m | 71.5 | 3.30 ddd (9.6, 6.0, 3.0) | 71.7 |
| 5ʹ | 3.11 t (9.0) | 75.6 | 3.34 m | 78.0 | 3.12 m | 78.2 |
| 6ʹa | 3.83 d (11.4) | 67.7 | 3.90 dd (11.4, 1.8) | 68.5 | 3.80 ddd (11.4, 4.8, 3.0) | 62.8 |
| 6ʹb | 3.40 dd (11.4, 7.2) | 3.55 dd (11.4, 6.0) | 3.58 ddd (11.4, 6.6, 6.0) | |||
| 1ʺ | 4.86 d (3.0) | 109.3 | 4.93 d (2.4) | 111.0 | ||
| 2ʺ | 3.74 (1.8) | 75.9 | 3.84 d (2.4) | 78.0 | ||
| 3ʺ | 78.8 | 80.5 | ||||
| 4ʺa | 3.84 d (9.0) | 73.2 | 3.89 d (9.6) | 75.0 | ||
| 4ʺb | 3.57 d (9.0) | 3.69 d (9.6) | ||||
| 5ʺ | 3.31 m | 63.1 | 3.52 s | 65.6 | ||
a
NMR data (δ) were measured at 600 MHz for 1H NMR and 150 MHz for 13C NMR in DMSO-d6 for 1, in MeOH-d4 for 2, and in acetone-d6 for 3, respectively. Proton coupling constants (J) in Hz are given in parentheses. The assignments were based on 1H–1H COSY, HSQC, and HMBC experiments.
b
1H NMR data for hydroxyl protons of 3: δH 4.23 (1H, brs, OH-4ʹ), 4.21 (1H, d, J=3.0 Hz, OH-2ʹ), 4.12 (1H, d, J=3.0 Hz, OH-3ʹ), 3.40 (1H, t, J=6.6 Hz, OH-6ʹ).