Table 1.
NMR spectroscopic data for compounds 1–3 in DMSO-d6.
| Position | 1 1 | 2 2 | 3 3 | |||
|---|---|---|---|---|---|---|
| δC | δH, m (J in Hz) | δC | δH, m (J in Hz) | δC | δH, m (J in Hz) | |
| 1 | 50.9 | 4.39, ovl | 50.9 | 4.39, ovl | 50.8 | 4.43, ovl |
| 2 | 36.2 | 2.30, dd (15.9, 8.8) | 36.2 | 2.29, m | 36.3 | 2.29, dd (15.7, 8.4) |
| 2.13, dd (15.9, 4.6) | 2.13, dd (16.3, 5.0) | 2.16, dd (15.7, 5.4) | ||||
| 3 | 170.5 | 170.6 | 170.6 | |||
| 4 | 173.4 | 173.4 | 173.4 | |||
| 1-NH | 7.78, s | 7.78, d (4.2) | 7.72, d (4.1) | |||
| 3-NH2 | 7.34, s | 7.35, s | 7.33, ovl | |||
| 6.92, ovl | 6.91, ovl | 6.92, s | ||||
| 5 | 56.3 | 4.03, m | 56.3 | 4.02, m | 56.3 | 4.02, m |
| 6 | 34.9 | 2.97, br d (10.6) | 34.9 | 2.97, dd (14.5, 3.5) | 34.9 | 2.96, dd (14.3, 3.4) |
| 2.75, dd (14.1, 10.6) | 2.74, dd (14.5, 11.4) | 2.75, dd (14.3, 10.5) | ||||
| 7 | 128.0 | 128.0 | 128.0 | |||
| 8 | 129.8 | 7.03, d (8.4) | 129.8 | 7.03, d (8.8) | 129.8 | 7.03, d (8.4) |
| 9 | 115.1 | 6.66, d (8.3) | 115.1 | 6.66, d (8.7) | 115.1 | 6.66, d (8.4) |
| 10 | 155.8 | 155.8 | 155.8 | |||
| 11 | 115.1 | 6.66, d (8.3) | 115.1 | 6.66, d (8.7) | 115.1 | 6.66, d (8.4) |
| 12 | 129.8 | 7.03, d (8.4) | 129.8 | 7.03, d (8.8) | 129.8 | 7.03, d (8.4) |
| 13 | 171.3 | 171.3 | 171.2 | |||
| 5-NH | 8.69, s | 8.69, d (6.3) | 8.72, ovl | |||
| 10-OH | 9.21, s | 9.21, s | 9.19, s | |||
| 14 | 50.9 | 4.48, m | 50.9 | 4.48, m | 49.6 | 4.43, ovl |
| 15 | 36.2 | 2.59, dd (15.5, 10.0) | 36.2 | 2.59, dd (15.6, 10.6) | 36.0 | 2.59, dd (15.5, 9.6) |
| 2.50, ovl | 2.50, ovl | 2.49, ovl | ||||
| 16 | 171.1 | 171.1 | 171.2 | |||
| 17 | 171.2 | 171.2 | 171.1 | |||
| 14-NH | 8.07, d (7.1) | 8.07, d (8.2) | 8.06, d (6.6) | |||
| 16-NH2 | 7.21, ovl | 7.21, s | 7.22, s | |||
| 6.89, ovl | 6.89, ovl | 6.88, s | ||||
| 18 | 49.6 | 4.51, dd (14.1, 8.6) | 49.6 | 4.51, m | 49.6 | 4.51, dd (14.1, 8.5) |
| 19 | 26.7 | 2.00, m | 26.7 | 1.99, ovl | 26.5 | 2.02, ovl |
| 1.71, m | 1.72, m | 1.74, ovl | ||||
| 20 | 30.5 | 2.09, ovl | 30.5 | 2.09, ovl | 30.6 | 2.10, ovl |
| 21 | 174.0 | 174.0 | 174.1 | |||
| 22 | 171.2 | 171.1 | 170.9 | |||
| 18-NH | 6.92, ovl | 6.92, ovl | 6.98, d (7.8) | |||
| 21-NH2 | 7.10, s | 7.11, s | 7.13, s | |||
| 6.85, ovl | 6.85, ovl | 6.86, s | ||||
| 23 | 59.7 | 4.28, t (7.9) | 59.7 | 4.28, t (8.7) | 60.1 | 4.17, ovl |
| 24 | 37.5 | 2.03, m | 37.5 | 2.03, m | 29.0 | 2.13, ovl |
| 1.86, m | 1.86, m | 1.77, m | ||||
| 25 | 68.7 | 4.39, ovl | 68.7 | 4.39, ovl | 24.6 | 2.00, ovl |
| 1.88, m | ||||||
| 26 | 55.7 | 3.82, br d (6.9) | 55.6 | 3.82, dd (10.1, 3.4) | 47.2 | 3.78, m |
| 3.69, ovl | 3.69, ovl | 3.74, m | ||||
| 27 | 172.6 | 172.6 | 172.7 | |||
| 25-OH | 5.22, s | 5.23, d (2.9) | ||||
| 28 | 49.7 | 4.43, m | 49.7 | 4.43, m | 49.7 | 4.43, ovl |
| 29 | 35.2 | 2.70, dd (15.5, 5.0) | 35.2 | 2.70, dd (16.5, 5.7) | 35.2 | 2.71, dd (15.7, 5.4) |
| 2.43, dd (15.5, 7.5) | 2.43, dd (16.5, 8.1) | 2.47, ovl | ||||
| 30 | 171.8 | 171.8 | 171.8 | |||
| 31 | 170.8 | 170.8 | 170.8 | |||
| 28-NH | 8.79, d (6.8) | 8.80, d (8.0) | 8.72, ovl | |||
| 30-NH2 | 7.37, s | 7.38, s | 7.38, s | |||
| 6.85, ovl | 6.85, ovl | 6.85, s | ||||
| 32 | 56.3 | 4.17, dd (11.7, 7.0) | 56.3 | 4.17, dd (12.3, 7.3) | 56.2 | 4.17, ovl |
| 33 | 61.4 | 3.69, ovl | 61.4 | 3.69, ovl | 61.4 | 3.66, t (5.5) |
| 3.65, m | 3.65, ovl | |||||
| 34 | 170.5 | 170.5 | 170.3 | |||
| 32-NH | 7.40, s | 7.40, ovl | 7.33, ovl | |||
| 33-OH | 4.87, t (5.5) | 4.88, t (6.0) | 4.87, t (5.9) | |||
| 35 | 45.2 | 3.99, m | 45.2 | 3.99, m | 45.3 | 3.98, m |
| 36 | 41.9 | 2.35, m | 41.9 | 2.35, m | 41.8 | 2.34, ovl |
| 37 | 171.3 | 171.3 | 171.2 | |||
| 38 | 34.6 | 1.43, m | 34.6 | 1.40, m | 34.6 | 1.41, m |
| 1.40, m | ||||||
| 39 | 25.3 | 1.24, ovl | 25.3 | 1.24, ovl | 25.4 | 1.24, ovl |
| 1.13, ovl | 1.11, ovl | 1.13, ovl | ||||
| 40–46 | 28.6–29.3 | 1.24, ovl | 28.6–26.5 | 1.24, ovl | 28.6–29.3 | 1.24, ovl |
| 47 | 26.8 | 1.24, ovl | 36.0 | 1.26, ovl | 26.8 | 1.24, ovl |
| 1.13, ovl | 1.08, m | 1.13, ovl | ||||
| 48 | 38.5 | 1.24, ovl | 33.7 | 1.27, ovl | 38.5 | 1.24, ovl |
| 1.13, ovl | 1.13, ovl | |||||
| 49 | 27.4 | 1.49, m | 28.9 | 1.24, ovl | 27.4 | 1.49, m |
| 1.09, ovl | ||||||
| 50 | 22.5 | 0.84, d (6.6) | 11.2 | 0.82, ovl | 22.6 | 0.84, d (6.6) |
| 51 | 22.5 | 0.84, d (6.6) | 19.1 | 0.82, ovl | 22.6 | 0.84, d (6.6) |
| 35-NH | 7.21, ovl | 7.21, s | 7.14, ovl | |||
1 900 MHz for 1H and 225 MHz for 13C NMR data; 2 700 MHz for 1H and 175 MHz for 13C NMR data; 3 800 MHz for 1H and 200 MHz for 13C NMR data; Ovl: overlapped with other signals.