Table 1.
1H-(500 MHz, δ in ppm, J in Hz) and 13C-NMR (125 MHz, δ in ppm) data of compounds 1–4 in CD3OD.
| No. | 1 | 2 | 3 | 4 | ||||
|---|---|---|---|---|---|---|---|---|
| δH | δC | δH | δC | δH | δC | δH | δC | |
| 1 | a 1.53, m | 38.4 | a 1.47, m | 38.3 | a 1.42, m | 38.0 | 215.4 | |
| b 2.52, m | b 2.53, dt (13.3, 5.0) | b 2.46, m | ||||||
| 2 | a 2.26, m | 30.8 | a 2.29, dt (13.3, 3.5) | 30.7 | a 2.27, dt (13.3, 3.3) | 30.5 | α 2.29, dd (11.9, 4.9) | 44.8 |
| b 2.66, dt (12.9, 5.2) | b 2.74, dt (13.0, 5.0) | b 2.74, dt (13.3, 5.1) | β 3.12, t (11.9) | |||||
| 3 | 180.2 | 178.3 | 177.9 | 3.82, dd (12.1, 4.9) | 73.5 | |||
| 4 | 149.3 | 149.3 | 149.3 | 44.1 | ||||
| 5 | 2.05, dd (12.7, 2.8) | 53.0 | 2.04, dd (12.8, 2.9) | 53.1 | 2.04, dd (12.8, 2.9) | 53.1 | 1.39, m | 47.9 |
| 6 | α 1.86, m | 27.4 | α 1.85, m | 27.4 | α 1.85, m | 27.5 | α 1.57, m | 18.6 |
| β 1.45, m | β 1.49, m | β 1.47, m | β 1.57, m | |||||
| 7 | α 1.59, m | 35.8 | α 1.59, dt (13.0, 3.3) | 35.8 | α 1.59, dt (12.9, 3.3) | 35.7 | α 1.55, m | 33.3 |
| β 1.22, m | β 1.21, m | β 1.22, m | β 1.29, m | |||||
| 8 | 40.9 | 40.9 | 40.9 | 40.5 | ||||
| 9 | 1.95, m | 45.4 | 1.95, m | 45.4 | 1.93, m | 45.5 | 2.40, m | 40.8 |
| 10 | 41.9 | 41.9 | 41.9 | 53.6 | ||||
| 11 | α 2.46, m | 33.8 | α 2.46, dt (12.5, 4.1) | 34.0 | α 2.42, m | 34.3 | α 2.44, m | 26.5 |
| β 1.34, m | β 1.35, m | β 1.37, m | β 1.88, ddd (12.5, 11.3, 5.4) | |||||
| 12 | 4.07, dt (10.7, 4.7) | 76.5 | 4.05, dt (10.8, 4.9) | 76.6 | 4.03, dt (10.8, 5.0) | 76.5 | 5.30, m | 125.3 |
| 13 | 1.70, m | 41.9 | 1.70, m | 41.9 | 1.70, m | 41.8 | 144.0 | |
| 14 | 51.4 | 51.4 | 51.4 | 42.8 | ||||
| 15 | α 1.49, m | 32.3 | α 1.44, m | 32.3 | α 1.45, m | 32.4 | α 1.00, m | 29.6 |
| β 1.13, m | β 1.12, m | β 1.12, m | β 1.72, m | |||||
| 16 | α 1.99, m | 27.1 | α 1.98, m | 27.1 | α 1.98, m | 27.0 | α 2.25, m | 28.7 |
| β 1.81, m | β 1.80, m | β 1.80, m | β 1.59. m | |||||
| 17 | 1.92, m | 50.2 | 1.93, m | 50.2 | 1.92, m | 50.1 | 47.0 | |
| 18 | 1.06, s | 16.9 | 1.05, s | 16.9 | 1.05, s | 16.8 | 3.06, br s | 45.5 |
| 19 | 1.10, s | 20.6 | 1.09, s | 20.6 | 1.09, s | 20.5 | 3.27, d (3.6) | 82.4 |
| 20 | 87.8 | 87.8 | 87.9 | 36.1 | ||||
| 21 | 1.16, s | 25.5 | 1.16, s | 25.5 | 1.16, s | 25.2 | α 1.64, m | 29.6 |
| β 1.00, m | ||||||||
| 22 | α 1.73, m | 35.0 | α 1.74, m | 35.0 | α 1.73, m | 34.8 | α 1.62, m | 34.0 |
| β 1.65, m | β 1.67, m | β 1.66, m | β 1.78, m | |||||
| 23 | α 1.89, m | 26.1 | α 1.89, m | 26.1 | α 1.89, m | 26.1 | a 3.33, d (11.2) | 65.9 |
| β 1.31, m | β 1.31, m | β 1.32, m | b 3.50, d (11.2) | |||||
| 24 | 3.79, m | 84.9 | 3.79, m | 84.9 | 3.79, dd (7.8, 6.6) | 84.9 | 0.88, s | 13.2 |
| 25 | 72.7 | 72.6 | 72.8 | 1.35, s | 15.9 | |||
| 26 | 1.19, s | 26.6 | 1.19, s | 26.6 | 1.21, s | 26.8 | 0.85, s | 18.2 |
| 27 | 1.16, s | 24.4 | 1.16, s | 24.5 | 1.15, s | 24.6 | 1.33, s | 25.1 |
| 28 | a 4.72, d (1.4) | 114.1 | a 4.71, d (1.6) | 114.1 | a 4.70, d (1.6) | 114.0 | 182.9 | |
| b 4.85, d (1.4) | b 4.84, d (1.6) | b 4.84, d (1.6) | ||||||
| 29 | 1.77, s | 24.0 | 1.76, s | 24.0 | 1.76, s | 23.9 | 0.94, s | 28.7 |
| 30 | 1.00, s | 16.9 | 1.00, s | 16.9 | 0.99, s | 16.9 | 0.97, s | 25.2 |
| 1′ | 4.29, d (7.1) | 101.2 | 4.28, d (7.1) | 101.4 | 4.36, d (7.7) | 100.4 | ||
| 2′ | 3.50, dd (9.6, 7.1) | 72.8 | 3.50, dd (9.6, 7.1) | 72.8 | 3.18, dd (9.3, 7.7) | 75.3 | ||
| 3′ | 3.46, dd (9.6, 3.3) | 74.6 | 3.46, dd (9.6, 3.3) | 74.6 | 3.29, m | 77.8 | ||
| 4′ | 3.77, m | 70.4 | 3.77, m | 70.3 | 3.00, t (9.1) | 77.1 | ||
| 5′ | 3.54, dd (12.7, 0.8) | 67.8 | 3.54, dd (12.7, 1.1) | 67.7 | 3.26, m | 73.0 | ||
| 3.88, dd (12.7, 1.9) | 3.88, dd (12.7, 1.9) | |||||||
| 6′ | 1.26, d (6.1) | 18.1 | ||||||
| OCH3 | 3.64, s | 52.1 | 3.63, s | 52.0 | ||||