Table 1.
1H- and 13C-NMR spectroscopic data for compounds 1–4 in CD3OD.
| Position | 1 | 2 | 3 | 4 | ||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | |||||||||
| 1 | 5.90 d (3.6) | 95.3 | 5.55 d (4.8) | 93.9 | 5.56 d (1.4) | 92.4 | 5.48 d (2.2) | 95.2 | ||||||||
| 3 | 7.57 d (1.4) | 154.5 | 7.47 d (1.0) | 152.1 | 7.38 d (1.2) | 150.9 | 7.41 d (1.2) | 153.2 | ||||||||
| 4 | 108.6 | 110.7 | 111.1 | 111.9 | ||||||||||||
| 5 | 3.48 ddd (8.8, 2.9, 1.4) | 40.1 | 3.52 ddd (9.0, 3.6, 1.0) | 37.1 | 2.70 ddd (11.2, 4.8, 1.2) | 34.3 | 2.82 ddd (10.9, 5.2, 1.2) | 38.3 | ||||||||
| 6 | 5.51 dd (5.6, 2.9) | 79.9 | 5.52 ddd (7.4, 4.2, 3.6) | 78.4 | 3.48 dd (8.0, 4.8) | 80.5 | 4.06 dd (5.2, 4.4) | 79.5 | ||||||||
| 7 | α: 2.27 dd (15.4, 5.6) β: 2.51 d (15.4) | 45.0 | β: 1.93 dd (14.0, 4.2) α: 2.34 dd (14.0, 7.4) | 46.4 | 3.73 d (8.0) | 84.4 | 3.60 d (4.4) | 81.2 | ||||||||
| 8 | 89.8 | 79.6 | 76.7 | 80.8 | ||||||||||||
| 9 | 3.09 dd (8.8, 3.6) | 50.4 | 2.54 dd (9.0, 4.8) | 50.6 | 2.53 dd (11.2, 1.4) | 45.7 | 2.54 dd (10.9, 2.2) | 47.6 | ||||||||
| 10 | 1.63 s | 21.8 | 1.37 s | 21.9 | 1.03 s | 16.5 | 1.27 s | 23.1 | ||||||||
| 11 | 168.4 | 167.7 | 168.7 | 170.6 | ||||||||||||
| OCH3 | 3.67 s | 51.9 | 3.56 s | 50.4 | 3.72 s | 50.8 | 3.73 s | 52.0 | ||||||||
| 8-OAc | 1.92 s | 22.3, 172.6 | ||||||||||||||
| 1' | 4.71 d (8.0) | 100.2 | 4.71 d (8.0) | 98.9 | 4.66 d (8.0) | 98.3 | 4.69 d (8.0) | 100.2 | ||||||||
| 2' | 3.22 dd (9.2, 8.0) | 74.7 | 3.20 dd (9.0, 8.0) | 73.4 | 3.19 dd (9.2, 8.0) | 73.4 | 3.21 dd (9.2, 8.0) | 74.6 | ||||||||
| 3' | 3.30–3.49 m | 77.9 | 3.37 t (9.0) | 74.6 | 3.41 m | 76.6 | 3.41 m | 77.8 | ||||||||
| 4' | 3.30–3.49 m | 71.4 a | 3.22 t (9.0) | 70.6 | 3.41 m | 70.4 | 3.41 m | 71.8 | ||||||||
| 5' | 3.30–3.49 m | 78.5 | 3.35 m | 76.6 | 3.62 m | 74.6 | 3.68 m | 75.8 | ||||||||
| 6' | 3.66 dd (12.0, 5.6) c 3.79 dd (12.0, 2.3) c | 62.5 b | 3.64 dd (11.8, 6.3) 3.92 dd (11.8, 2.4) | 63.8 | 4.39 dd (12.0, 5.4) 4.66 dd (12.0, 2.0) | 63.8 | 4.44 dd (12.0, 6.1) 4.66 dd (12.0, 2.1) | 65.0 | ||||||||
| 1" | 127.4 | 120.7 | 120.0 | 121.2 | ||||||||||||
| 2", 6" | 7.38 s | 108.7 | 7.39 s | 108.7 | 7.33 s | 107.1 | 7.35 s | 108.3 | ||||||||
| 3", 5" | 154.3 | 147.8 | 147.8 | 148.9 | ||||||||||||
| 4" | 140.6 | 140.6 | 140.6 | 142.1 | ||||||||||||
| 1"-C=O | 166.8 | 166.8 | 166.8 | 167.9 | ||||||||||||
| 3",5"-OCH3 | 3.93 s | 57.3 | 3.89 s | 55.7 | 3.89 s | 55.7 | 3.88 s | 56.9 | ||||||||
| 1'" | 5.13 d (7.8) | 104.3 | ||||||||||||||
| 2'" | 3.52 dd (9.2, 7.8) | 75.7 | ||||||||||||||
| 3'" | 3.30–3.49 m | 77.9 | ||||||||||||||
| 4'" | 3.30–3.49 m | 71.6 a' | ||||||||||||||
| 5'" | 3.30–3.49 m | 78.5 | ||||||||||||||
| 6'" | 3.69 dd (12.2, 5.6) c' 3.94 dd (12.0, 2.2) c' | 63.0 b' | ||||||||||||||
a and a', b and b', c and c': Assignments may be interchangeable. m: Overlapping or irresolvable peak. 1H- and 13C-NMR data (δ) were measured in CD3OD at 400 and 100 MHz.