Table 2.
The NMR spectral data (δ) for compounds 3–8a.
No |
3b |
4 |
5c |
6d |
7 |
8 |
||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
δH | δC | δH | δC | δH | δC | δH | δC | δH | δC | δH | δC | |
1 | 11.29 | 10.82 s | 10.92 s | |||||||||
2 | 127.9 | 7.39 s | 126.8 | 7.45 s | 124.7 | 139.0 | 7.20 s | 124.6 | 137.5 | |||
3 | 135.5 | 105.8 | 104.5 | 99.8 | 108.3 | 109.1 | ||||||
3a | 121.5 | 127.3 | 125.5 | 116.1 | 127.8 | 127.9 | ||||||
4 | 7.91 brd (7.8) | 120.8 | 7.75 brd (8.4) | 120.5 | 7.69 brd (7.8) | 120.8 | 154.3 | 7.59 brd (7.8) | 119.5 | 7.52 brd (7.8) | 120.1 | |
5 | 7.03 dt (1.2, 7.8) | 120.7 | 7.00 dt (1.2, 8.4) | 120.5 | 7.06 dt (1.2, 7.8) | 120.7 | 6.48 d (8.0) | 99.7 | 6.92 brt (7.8) | 117.9 | 6.91 dt (1.2, 7.8) | 118.2 |
6 | 7.17 dt (1.2, 7.8) | 124.8 | 7.07 dt (1.2, 8.4) | 122.8 | 7.17 dt (1.2, 7.8) | 123.2 | 7.00 t (8.0) | 123.3 | 7.01 brt (7.8) | 120.4 | 7.04 dt (1.2, 7.8) | 121.8 |
7 | 7.33 brd (7.8) | 113.0 | 7.31 brd (8.4) | 112.4 | 7.37 brd (7.8) | 108.9 | 6.92 d (8.0) | 105.4 | 7.30 brd (7.8) | 110.9 | 7.29 brd (7.8) | 111.6 |
7a | 133.9 | 137.9 | 133.4 | 135.6 | 135.8 | 133.8 | ||||||
8 | 5.39 s | 50.9 | 4.21 s | 49.5 | 4.20 s | 14.0 | 3.86 s | 48.4 | 3.66 s | 34.4 | ||
9 | 118.4 | 119.8 |
NMR data (δ) were measured in CD3OD for 3–5 and in DMSO-d6 for 6–8, at 600 MHz for 1H and 150 MHz for 13C of 3–5, 7, and 8 and at 500 MHz for 1H and 125 MHz for 13C of 6, respectively. Proton coupling constants (J) in Hz are given in parentheses. The assignments were based on 1H—1H COSY, HSQC, and HMBC experiments.
Data for glucopyranosyl in 3: δH 4.81 (1 H, d, J = 7.8 Hz, H-1ʺ), 3.58 (1 H, dd, J = 9.6, 7.8 Hz, H-2ʺ), 3.44 (1 H, t, J = 9.6 Hz, H-3ʺ), 3.45 (1 H, t, J = 9.6 Hz, H-4ʺ), 3.28 (1 H, m, H-5ʺ), 3.91 (1 H, dd, J = 12.0, 2.4 Hz, H-6ʺa), 3.79 (1 H, dd, J = 12.0, 4.8 Hz, H-6ʺb); δC 107.4 (C-1ʺ), 75.3 (C-2ʺ), 77.7 (C-3ʺ), 71.2 (C-4ʺ), 78.3 (C-5ʺ), 62.5 (C-6ʺ).
Data for methoxy in 5: δH 4.07 (3 H, s); δC 66.2.
Data for methoxy in 6: δH 3.85 (3 H, s); δC 55.3.