Table 1.
1H NMR and 13C NMR spectral data (δ) for compounds 1−7.a.
| No. |
1 |
2 |
3b |
4 |
5 |
6 |
7 |
|||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| δH | δC | δH | δC | δH | δC | δH | δC | δH | δC | δH | δC | δH | δC | |
| 1 | 173.4 | 172.7 | 172.6 | 173.0 | 172.5 | 176.7 | 174.3 | |||||||
| 2 | 4.01 dd (9.0, 3.6) | 58.9 | 3.97 dd (9.0, 3.0) | 59.4 | 3.90 dd (8.4, 3.6) | 59.2 | 4.19 m | 70.4 | 4.16 m | 70.4 | 4.26 brs | 72.1 | 4.11 m | 68.6 |
| 3a | 2.33 m | 23.4 | 2.28 m | 23.4 | 2.22 m | 23.3 | 2.67 dd (13.5, 5.5) | 34.5 | 2.67 dd (14.0, 5.5) | 34.5 | 2.83 brd (13.8) | 36.3 | 1.82 m | 33.7 |
| 3b | 2.08 m | 2.01 m | 1.99 m | 2.58 dd (13.5, 6.5) | 2.57 dd (14.0, 6.0) | 2.69 dd (13.8, 6.6) | 1.76 m | |||||||
| 4a | 2.43 m | 30.2 | 2.38 m | 30.3 | 2.37 m | 30.5 | 2.41 m | 26.3 | ||||||
| 4b | 2.36 m | 2.30 m | 2.26 m | |||||||||||
| 5 | 175.5 | 174.9 | 174.9 | |||||||||||
| 1′ | 127.9 | 128.1 | 127.9 | 128.3 | 128.3 | 130.4 | 128.5 | |||||||
| 2′ | 7.08 d (8.4) | 130.5 | 7.05 d (8.4) | 130.5 | 6.88 d (2.4) | 131.3 | 7.09 d (8.0) | 130.0 | 7.09 d (8.5) | 130.0 | 7.15 d (8.4) | 131.3 | 7.08 d (8.5) | 129.9 |
| 3′ | 6.79 d (8.4) | 116.1 | 6.78 d (8.4) | 116.1 | 129.4 | 6.69 d (8.0) | 115.1 | 6.69 d (8.5) | 115.1 | 6.71 d (8.4) | 116.1 | 6.68 d (8.5) | 115.1 | |
| 4′ | 157.7 | 157.7 | 155.3 | 156.2 | 156.2 | 157.5 | 156.2 | |||||||
| 5′ | 6.79 d (8.4) | 116.1 | 6.78 d (8.4) | 116.1 | 6.79 d (8.4) | 116.0 | 6.69 d (8.0) | 115.1 | 6.69 d (8.5) | 115.1 | 7.15 d (8.4) | 116.1 | 6.68 d (8.5) | 115.1 |
| 6′ | 7.08 d (8.4) | 130.5 | 7.05 d (8.4) | 130.5 | 6.87 dd (8.4, 2.4) | 128.0 | 7.09 d (8.0) | 130.0 | 7.09 d (8.5) | 130.0 | 6.71 d (8.4) | 131.3 | 7.08 d (8.5) | 129.9 |
| 7′a | 4.94 d (15.0) | 45.2 | 4.82 d (15.0) | 45.3 | 4.80 d (14.4) | 45.3 | 3.67 s | 35.3 | 3.67 s | 35.3 | 3.73 s | 37.1 | 3.60 s | 34.5 |
| 7′b | 3.85 d (15.0) | 3.87 d (15.0) | 3.79 d (14.4) | |||||||||||
| OCH3 | 3.63 s | 51.6 | 3.62 s | 51.5 | ||||||||||
| OCH2CH3 | 4.11 q (7.2) | 61.7 | 4.08 q (7.2) | 61.7 | 4.09 q (7.0) | 60.2 | ||||||||
| OCH2CH3 | 1.21 t (7.2) | 14.4 | 1.18 t (7.2) | 14.4 | 1.19 t (7.0) | 14.1 | ||||||||
| 2-OH | 5.75 d (6.0) | 5.71 d (6.0) | 5.49 d (6.0) | |||||||||||
| 4′-OH | 8.31 s | 8.44 s | 9.32 s | 9.33 s | 9.34 s | |||||||||
a
NMR data (δ) were measured in Me2CO-d6 for 1−3 at 600 MHz for 1H and at 150 MHz for 13C, in DMSO-d6 for 4, 5, and 7 at 500 MHz for 1H and at 125 MHz for 13C and in MeOH-d4 for 6 at 600 MHz for 1H and at 150 MHz for 13C. Proton coupling constants (J) in Hz are given in parentheses. The assignments were based on DEPT, 1H-1H COSY, HSQC, and HMBC experiments.
b
Data for 4″-hydroxybenzyl in 3: δH 8.16 (s, 1H, OH-4″), 7.05 (d, 2H, J=8.4 Hz, H-2″/6″), 6.71 (d, 2H, J=8.4 Hz, H-3″/5″), 3.82 (s, 2H, H2-7″); δC 132.7 (C-1″), 130.6 (C-2″/6″), 115.8 (C-3″/5″), 156.4 (C-4″), 35.4 (C-7″).