Table 1. 1H and 13C NMR spectroscopic data for compounds 1-6a.
Position | 1 and 2b | 3 and 4b | 5 and 6c | |||
---|---|---|---|---|---|---|
δC, type | δH (J in Hz) | δC, type | δH (J in Hz) | δC, type | δH (J in Hz) | |
1 | 151.4, C | 149.1, C | 147.4, C | |||
2 | 118.5, CH | 6.67, br s | 123.6, C | 122.0, C | ||
3 | 123.6, C | 113.5, CH | 6.47, d (2.8) | 113.2, CH | 6.87, d (2.8) | |
4 | 118.4, CH | 6.67, br s | 151.6, C | 149.6, C | ||
5 | 149.4, C | 117.4, CH | 6.60, dd (8.6, 2.8) | 117.0, CH | 6.61, dd (8.4, 2.8) | |
6 | 114.8, CH | 6.94, br s | 117.4, CH | 6.67, d (8.6) | 117.1, CH | 6.66, d (8.4) |
1' | 108.7, C | 80.0, CH | 6.23, br s | 106.5, C | ||
2' | 147.9, CH | 7.40, br s | 151.0, CH | 7.35, br s | 145.9, CH | 7.38, d (1.0) |
3' | 136.7, C | 133.7, C | 134.9, C | |||
4' | 26.3, CH2 | 2.27, t (6.8) | 26.4, CH2 | 2.30, t (7.2) | 24.8, CH2 | 2.20, t (7.6) |
5' | 25.9, CH2 | 1.59, m | 26.1, CH2 | 1.61, m | 24.2, CH2 | 1.49, m |
6' | 31.5, CH2 | 1.31, m | 31.6, CH2 | 1.43, m | 30.0, CH2 | 1.22, m |
7' | 41.0, CH | 1.47, m | 41.1, CH | 1.50, m | 39.4, CH | 1.37, o |
8' | 31.7, CH2 | 1.40, m | 31.7, CH2 | 1.34, m | 30.3, CH2 | 1.36, o |
9' | 26.1, CH2 | 2.06, td (7.2, 7.2) | 26.2, CH2 | 2.08, m | 24.5, CH2 | 1.98, td (7.6, 7.2) |
10' | 130.8, CH | 5.49, t (6.6) | 130.8, CH | 5.50, br s | 129.1, CH | 5.46, t (6.8) |
11' | 131.7, C | 131.7, C | 129.9, C | |||
12' | 71.2, CH2 | 4.55, br s | 71.2, CH2 | 4.55, br s | 69.0, CH2 | 4.50, br s |
13' | 14.3, CH3 | 1.68, s | 14.3, CH3 | 1.69, d (3.7) | 13.7, CH3 | 1.61, s |
14' | 173.6, C | 176.9, C | 171.0, C | |||
15' | 65.4, CH2 | 3.46, br d (3.7) | 65.5, CH2 | 3.48, br d (4.8) | 63.0, CH2 | 3.29, br d (4.4) |
1'' | 169.3, C | 169.3, C | 166.4, C | |||
2'' | 115.3, CH | 6.33, d (15.6) | 115.4, CH | 6.33, d (16.0) | 114.0, CH | 6.40, d (16.0) |
3'' | 146.7, CH | 7.60, d (15.6) | 146.7, CH | 7.60, d (16.0) | 144.7, CH | 7.55, d (16.0) |
4'' | 127.3, C | 127.3, C | 124.9, C | |||
5''9'' | 131.3, CH2 | 7.45, d (8.4) | 131.3, CH2 | 7.45, d (8.6) | 130.3, CH2 | 7.54, d (8.4) |
6''8'' | 117.0, CH2 | 6.80, d (8.4) | 117.0, CH2 | 6.79, d (8.6) | 115.8, CH2 | 6.78, d (8.4) |
7'' | 161.4, C | 161.4, C | 160.0, C | |||
OCH3 | 52.3, CH3 | 3.27, s | 51.0, CH3 | 3.16, s |
a 1H NMR, 400 MHz; 13C NMR, 100 MHz. The assignments were based on HSQC and HMBC experiments. The 1H and 13C NMR data were identical for each pair of enantiomers.
b Measured in CD3OD.
c Measured in DMSO-d6.