Table 2.
1H and 13C-NMR data of compounds 3–5 (CDCl3, 500MHz for 1H-NMR, 125MHz for 13C-NMR) a.
| No. | 3 | 4 | 5 | |||
|---|---|---|---|---|---|---|
| δC, mult. | δH (int., mult., J in Hz) | δC, mult. | δH (int., mult., J in Hz) | δC, mult. | δH (int., mult., J in Hz) | |
| 1 | 62.2 (t) | 3.75 (1H, m), 3.89 (1H, br d, 10.0) |
61.8 (t) | 3.71 (1H, d, 11.0), 3.86 (1H, d, 11.2) |
61.9 (t) | 3.74 (1H, m), 3.87 (1H, m) |
| 2 | 54.4 (d) | 3.91 (1H, br d, 10.0) | 54.5 (d) | 3.92 (1H, m) | 56.1 (d) | 3.93 (1H, m) |
| 3 | 74.2 (d) | 4.28 (1H, m) | 74.1 (d) | 4.28 (1H, br s) | 74.1 (d) | 4.28 (1H, m) |
| 4 | 129.2 (d) | 5.54 (1H, m) | 128.9 (d) | 5.51 (1H, dd, 15.5, 6.0) | 128.6 (d) | 5.53 (1H, br d, 14.0) |
| 5 | 133.3 (d) | 5.77 (1H, m) | 133.5 (d) | 5.77 (1H, m) | 134.3 (d) | 5.65 (1H, dt, 14.3, 6.5) |
| 6 | 31.9 (t) | 2.16 (2H, t, 2.9) | 32.6 (t) | 1.96 (2H, q-like, 6.2) | 32.3 (t) | 2.05 (2H, m) |
| 7 | 32.1 (t) | 2.04 (2H, q, 7.1) | 32.4 (t) | 2.11 (2H, m) | 29.2–29.7 (t) | 1.26 (2H, br s) b |
| 8 | 133.5 (d) | 5.59 (1H, dt, 15.0, 6.0) | 131.3 (d) | 5.41 (1H, m) | 29.2–29.7 (t) | 1.26 (2H, br s) b |
| 9 | 130.0 (d) | 5.98 (1H, m) | 129.0 (d) | 5.38 (1H, m) | 29.2–29.7 (t) | 1.26 (2H, br s) b |
| 10 | 131.2 (d) | 6.00 (1H, m) | 32.2 (t) | 2.07 (2H, m) | 29.2–29.7 (t) | 1.26 (2H, br s) b |
| 11 | 130.7 (d) | 5.52 (1H, m) | 29.3–29.7 (t) | 1.26 (2H, br s) b | 29.2–29.7 (t) | 1.26 (2H, br s) b |
| 12 | 32.1 (t) | 2.16 (2H, t, 2.9) | 29.3–29.7 (t) | 1.26 (2H, br s) b | 29.2–29.7 (t) | 1.26 (2H, br s) b |
| 13 | 32.6 (t) | 2.04 (2H, q, 7.1) | 29.3–29.7 (t) | 1.26 (2H, br s) b | 29.2–29.7 (t) | 1.26 (2H, br s) b |
| 14 | 29.4 (t) | 1.36 (2H, m) | 29.3–29.7 (t) | 1.26 (2H, br s) b | 29.2–29.7 (t) | 1.26 (2H, br s) b |
| 15 | 29.2 (t) | 1.36 (2H, m) | 29.3–29.7 (t) | 1.26 (2H, br s) b | 29.2–29.7 (t) | 1.26 (2H, br s) b |
| 16 | 31.9 (t) | 1.26 (2H, br s) b | 32.0 (t) | 1.26 (2H, br s) b | 32.0 (t) | 1.26 (2H, br s) b |
| 17 | 22.7 (t) | 1.26 (2H, br s) b | 22.7 (t) | 1.26 (2H, br s) b | 22.7 (t) | 1.26 (2H, br s) b |
| 18 | 14.1 (q) | 0.87 (3H, t, 7.1) | 14.1 (q) | 0.88(3H, t, 7.0) | 14.1 (q) | 0.88(3H, t, 7.1) |
| 1′ | 175.1 (s) | - | 173.0 (s) | - | 173.0 (s) | - |
| 2′ | 72.4 (d) | 4.12 (1H, dd, 7.8, 3.4) | 43.4 (t) | a 2.29 (1H, dd, 14.5, 9.5), | 43.3 (t) | a 2.31 (1H, m), b 2.41 (1H, m) |
| b 2.41 (1H, d, 14.3) | ||||||
| 3′ | 34.8 (t) | 2.16 (2H, t, 2.9) | 68.9 (d) | 4.00 (1H, m) | 68.9 (d) | 4.00 (1H, m) |
| 4′ | 31.8 (t) | 1.26 (2H, br s) b | 37.2 (t) | a 1.43 (1H, m), b 1.51 (1H, m) |
37.1 (t) | a 1.43 (1H, m), b 1.51 (1H, m) |
| 5′ | 25.1 (t) | 1.62 (2H, m) | 25.6 (t) | a 1.26 (1H, br s) b, b 1.43 (1H, m) |
25.6 (t) | a 1.30 (1H, m), b 1.43 (1H, m) |
| 6′~13′ | 29.1–29.7 (t) | 1.26 (16H, br s) b | 29.3–29.7 (t) | 1.26 (16H, br s) b | 29.2–29.7 (t) | 1.26 (16H, br s) b |
| 14′ | 29.1–29.7 (t) | 1.26 (2H, br s) b | 32.0 (t) | 1.26 (2H, br s) b | 32.0 (t) | 1.26 (2H, br s) b |
| 15′ | 29.1–29.7 (t) | 1.26 (2H, br s) b | 22.7 (t) | 1.26 (2H, br s) b | 22.7 (t) | 1.26 (2H, br s) b |
| 16′ | 31.9 (t) | 1.26 (2H, br s) b | 14.1 (q) | 0.88 (3H, t, 7.0) | 14.1 (q) | 0.88 (3H, t, 7.1) |
| 17′ | 22.7 (t) | 1.26 (2H, br s) b | - | - | - | - |
| 18′ | 14.1 (q) | 0.87 (3H, t, 7.1) | - | - | - | - |
| NH | - | 7.20 (1H, d, 7.9) | - | 6.76 (1H, d, 7.8) | - | 6.77 (1H, d, 7.8) |
a Assignments aided by DEPT, 1H-1H COSY, HSQC, HMBC and NOESY experiments; b overlapped with other signals.