Table 1.
1H (500 MHz) and 13C (125 MHz) NMR spectroscopic data of compounds 1–3 (CDCl3) a.
| Position | 1 | 2 | 3 | |||
|---|---|---|---|---|---|---|
| δC (ppm), type | δH (ppm) (J in Hz) | δC (ppm), type | δH (ppm) (J in Hz) | δC (ppm), type | δH (ppm) (J in Hz) | |
| 1 | 29.7, t | α, 1.39, m | 29.5, t | 1.59, m | 31.8, t | α, 1.97, m |
| β, 1.45, m | β, 1.58 m | |||||
| 2 | 23.4, t | α, 1.64, m | 22.9, t | α, 1.75, m | 23.1, t | α, 1.87, m |
| β, 1.85, m | β, 1.95, m | β, 1.98, m | ||||
| 3 | 77.2, d | 4.68, t (2.8) | 76.9, d | 4.71, t (2.5) | 78.8, d | 4.82, brd (3.2) |
| 4 | 36.2, s | 36.5, s | 37.6, s | |||
| 5 | 39.7, d | 1.99, dd (12.5, 1.1) | 42.6, d | 2.07, dd (7.5, 3.9) | 43.9, d | 1.94, m |
| 6 | 22.4, t | α, 1.89, m | 36.2, t | 2.35, m | 23.7, t | α, 2.14, brt (5.0) |
| β, 1.30, m | β, 2.08, m | |||||
| 7 | 74.0, d | 3.53, brs | 198.3, s | 119.4, d | 5.60, brd (5.9) | |
| 8 | 135.2, s | 142.5, s | 142.3, s | |||
| 9 | 140.0, s | 163.3, s | 145.8, s | |||
| 10 | 38.5, s | 39.2, s | 36.4, s | |||
| 11 | 21.0, t | 1.95, 2H, m | 22.2, t | α, 2.30, m | 114.8, d | 5.29, brd (5.9) |
| β, 2.14, m | ||||||
| 12 | 31.2, t | α, 1.34, m | 29.8, t | α, 1.38, m | 39.1, t | α, 2.08, m |
| β, 1.60, m | β, 1.59, m | β, 1.79, m | ||||
| 13 | 37.0, s | 38.0, s | 37.5, s | |||
| 14 | 41.7, s | 39.1, s | 40.4, s | |||
| 15 | 25.4, t | α, 2.18, m | 29.4, t | α, 2.43, m | 27.6, t | α, 1.63, m |
| β, 1.25, m | β, 1.59, m | β, 1.42, m | ||||
| 16 | 36.9, t | 1.56, 2H, m | 35.9, t | α, 1.39, m | 37.2, t | α, 1.76, m |
| β, 1.63, m | β, 1.49, m | |||||
| 17 | 31.1, s | 31.1, s | 31.9, s | |||
| 18 | 44.0, d | 1.59, m | 41.3, d | 1.66, m | 45.1, d | 1.68, m |
| 19 | 28.8, t | α, 1.84, m | 30.2, t | α, 1.63, m | 29.6, t | α, 1.76, m |
| β, 1.30, m | β, 1.29, dd (15.7, 3.9) | β, 1.30, m | ||||
| 20 | 31.9, s | 32.4, s | 29.9, s | |||
| 21 | 29.5, t | 1.51, 2H, m | 28.3, t | α, 1.56, m | 30.1, t | 1.63, 2H, m |
| β, 1.47, m | ||||||
| 22 | 35.7, t | α, 1.79, m | 38.5, t | α, 1.50, m | 33.0, t | α, 1.89, m |
| β, 0.97, m | β, 1.03, m | β, 0.95, m | ||||
| 23 | 27.2, q | 0.88, s | 26.7, q | 0.87, s | 28.0, q | 0.90, s |
| 24 | 22.3, q | 0.93, s | 21.4, q | 0.99, s | 21.6, q | 1.03, s |
| 25 | 18.2, q | 0.94, s | 18.0, q | 1.03, s | 21.1, q | 1.01, s |
| 26 | 26.1, q | 1.04, s | 26.7, q | 1.39, s | 21.2, q | 0.94, s |
| 27 | 18.9, q | 1.06, s | 18.3, q | 0.99, s | 19.9, q | 1.03, s |
| 28 | 31.2, q | 1.13, s | 30.6, q | 1.22, s | 31.4, q | 1.11, s |
| 29 | 73.0, t | a, 4.15, d (10.8) | 75.0, t | a, 4.05, d (10.5) | 74.2, t | a, 4.34, d (10.7) |
| b, 4.09, d (10.8) | b, 4.02, d (10.5) | b, 4.12, d (10.7) | ||||
| 30 | 29.7, q | 1.08, s | 26.5, q | 1.15, s | 31.3, q | 1.16, s |
| 3-OCO | 171.1, s | 170.6, s | 165.4, s | |||
| 1' | 21.5, q | 2.06, s | 21.3, q | 2.07, s | 123.1, s | |
| 2', 6' | 131.9, d | 7.85, 2H, dd (8.4, 2.8) | ||||
| 3', 5' | 115.3, d | 6.84, 2H, dd (8.4, 2.8) | ||||
| 4' | 160.8, s | |||||
| 29-OCO | 166.6, s | 166.8, s | 168.5, s | |||
| 1'' | 130.7, s | 130.6, s | 130.2, s | |||
| 2'', 6'' | 129.5, d | 8.06, 2H, dd (7.4, 1.3) | 129.5, d | 8.06, 2H, dd (8.0, 1.4) | 129.6, d | 8.04, 2H, dd (7.4, 1.4) |
| 3'', 5'' | 128.3, d | 7.46, 2H, tt (7.4, 1.3) | 132.8, d | 7.46, 2H, tt (8.0, 1.4) | 128.8, d | 7.46, 2H, tt (7.4, 1.4) |
| 4'' | 132.7, d | 7.57, tt (7.4, 1.3) | 128.4, d | 7.58, tt (8.0, 1.4) | 133.6, d | 7.56, tt (7.4, 1.4) |
| 7-OMe | 55.0, q | 3.24, s | ||||
| 4'-OH | 7.49, brs | |||||
a Assignments were based on 1H-1H COSY, HMQC, HMBC and NOESY spectroscopic data.