Table 1.
1H and 13C nuclear magnetic resonance (NMR) data of Compounds 1–3 in CD3OD a.
| Position | 1 | 2 | 3 | ||||||
|---|---|---|---|---|---|---|---|---|---|
| δ H | δ C | δ H | δ C | δ H | δ C | ||||
| 1 | 176.4 | s | 176.7 | s | 176.0 | s | |||
| 2 | 6.30 d (1.0) | 115.9 | d | 6.26 s | 114.9 | d | 6.17 s | 114.4 | d |
| 3 | 166.7 | s | 167.3 | s | 168.1 | s | |||
| 4 | 6.07 td (4.5, 1.0) | 84.6 | d | 6.04 td (5.0, 1.0) | 84.9 | d | 6.16 m | 85.5 | d |
| 5a | 2.92 dd (15.0, 5.0) | 38.7 | t | 2.86 dd (15.0, 5.0) | 38.9 | t | 2.85 dd (15.0. 6.0) | 38.8 | t |
| 5b | 3.24 dd (15.0, 4.5) | 3.20 dd (15.0, 4.0) | 3.24 dd (15.0, 3.5) | ||||||
| 1′ | 129.6 | s | 126.7 | s | 130.8 | s | |||
| 2′ | 6.85 d (8.5) | 131.9 | d | 6.78 d (8.5) | 131.9 | d | 7.00 d (8.5) | 131.7 | d |
| 3′ | 6.89 d (8.5) | 117.0 | d | 6.60 d (8.5) | 115.5 | d | 6.95 d (8.5) | 117.1 | d |
| 4′ | 158.0 | s | 157.0 | s | 157.9 | s | |||
| 5′ | 6.89 d (8.5) | 117.0 | d | 6.60 d (8.5) | 115.5 | d | 6.95 d (8.5) | 117.1 | d |
| 6′ | 6.85 d (8.5) | 131.9 | d | 6.78 d (8.5) | 131.9 | d | 7.00 d (8.5) | 131.7 | d |
| 1″ | 113.9 | s | 113.1 | s | 113.7 | s | |||
| 2″ | 158.5 | s | 158.5 | s | 158.1 | s | |||
| 3″ | 6.96 d (2.5) | 102.7 | d | 6.77 d (2.5) | 104.0 | d | 6.96 d (2.5) | 102.3 | d |
| 4″ | 164.8 | s | 163.0 | s | 165.0 | s | |||
| 5″ | 6.73 dd (8.5, 2.5) | 109.5 | d | 6.60 dd (8.5, 2.5) | 110.9 | d | 6.74 dd (8.5, 2.5) | 109.9 | d |
| 6″ | 7.34 d (8.5) | 131.8 | d | 7.26 d (8.5) | 132.1 | d | 7.45 d (8.5) | 132.2 | d |
| 1‴ | 5.12 d (7.5) | 101.6 | d | 5.03 d (7.5) | 101.6 | d | 5.07 d (7.5) | 101.8 | d |
| 2‴ | 3.48 m | 74.6 | d | 3.49 m | 74.5 | d | 3.48 m | 74.4 | d |
| 3‴ | 3.42 m | 77.9 | d | 3.46 m | 78.3 | d | 3.48 m | 78.0 | d |
| 4‴ | 3.36 m | 71.1 | d | 3.40 m | 71.0 | d | 3.36 m | 71.2 | d |
| 5‴ | 3.52 m | 78.4 | d | 3.59 m | 76.9 | d | 3.55 m | 78.4 | d |
| 6‴a | 3.92 dd (12.0, 2.0) | 62.4 | t | 4.03 dd (11.5, 2.0) | 67.5 | t | 3.95 dd (12.0, 2.0) | 62.4 | t |
| 6‴b | 3.68 dd (12.0, 6.0) | 3.65 dd (11.5, 6.0) | 3.71 dd (12.0, 6.0) | ||||||
| 1⁗ | 4.84 d (7.5) | 102.1 | d | 4.70 d (1.0) | 102.1 | d | 4.85 d (7.5) | 102.1 | d |
| 2⁗ | 3.42 m | 74.8 | d | 3.88 m | 71.8 | d | 3.44 m | 74.6 | d |
| 3⁗ | 3.44 m | 77.8 | d | 3.69 dd (9.5, 3.5) | 72.0 | d | 3.48 m | 78.0 | d |
| 4⁗ | 3.38 m | 71.1 | d | 3.33 m | 73.8 | d | 3.44 m | 71.1 | d |
| 5⁗ | 3.48 m | 78.5 | d | 3.63 dd (9.6, 6.5) | 69.6 | d | 3.39 m | 78.3 | d |
| 6⁗a | 3.86 dd (12.0, 2.0) | 62.3 | t | 1.18 d (6.0) | 17.6 | q | 3.90 dd (12.0, 2.0) | 62.2 | t |
| 6⁗b | 3.68 dd (12.0, 6.0) | 3.69 dd (12.0, 6.0) | |||||||
| 4″-OCH3 | 3.88 s | 56.0 | q | 3.88 s | 55.8 | q | |||
a Signal multiplicity and coupling constants (Hz) are in given parentheses; the assignments were based on heteronuclear single quantum coherence (HSQC), HMBC, and 1H–1H COSY experiments.