Table 2.
NMR data for compounds 1, 2, 3 and 4 recorded at 600 MHz in DMSO-d6.
| 1 | 2 | 3 | 4 | |||||
|---|---|---|---|---|---|---|---|---|
| Posn. | δH mult (J in Hz) |
δC | δH mult (J in Hz) |
δC | δH mult (J in Hz) |
δC | δH mult (J in Hz) |
δC |
| 1 | 5.09 d (8.3) | 78.7 CH | 4.34 d (3.0) | 83.6 CH | 5.97 d (1.1) | 58.8 CH | 4.92 dd (2.3, 1.3) | 46.6 CH |
| 2 | 2.81 dd (9.6, 8.3) | 42.5 CH | 2.97 d (11.8) | 39.6 CH | 4.29 d (1.1) | 30.0 CH | 3.82 dd (2.7, 1.3) | 34.3 CH |
| 3 | 4.67 dd (9.6, 2.0) | 53.6 CH | 4.83 d (11.8) | 51.3 CH | 4.10 d (10.5) | 54.8 CH | 4.71 d (3.8) | 52.3 CH |
| 4 | 3.52 dd (9.8, 2.0) | 43.9 CH | 3.29 m | 44.6 CH | 3.83 d (10.5) | 48.9 CH | 3.87 dd (3.8, 2.4) | 46.3 CH |
| 5 | 4.60 dd (9.8, 5.5) | 64.9 CH | 4.57 dd (10.3, 5.0) | 65.3 CH | 4.76 dd (10.5, 9.6) | 60.3 CH | 5.23 dd (8.2, 2.4) | 65.1 CH |
| 6 | 4.64 d (5.5) | 58.4 CH | 4.50 d (5.0) | 59.2 CH | 5.11 d (9.6) | 60.6 CH | 5.29 d (8.2) | 56.3 CH |
| 1-OMe | N/A | N/A | 3.24 s | 56.1 CH3 | N/A | N/A | N/A | N/A |
| 7 | 155.4 C | 155.8 C | 153.0 C | 154.7 C | ||||
| 8 | 159.6 C | 159.9 C | –a | –a | ||||
| 2’ | 6.96 s | 126.2 CH | 7.03 s | 127.0 CH | 7.23 s | 124.3 CH | 7.29 s | 123.7 CH |
| 3’ | 110.9 C | 110.7 C | 108.4 C | 112.9 C | ||||
| 4’ | 7.15 d (8.5) | 121.0 CH | 7.20 d (8.5) | 122.1 CH | 7.47 d (8.4) | 120.3 CH | 7.53 d (8.5) | 120.2 CH |
| 5’ | 7.06 d (8.5) | 123.3 CH | 7.05 d (8.5) | 123.4 CH | 7.11 d (8.4) | 123.3 CH | 7.16 d (8.5) | 123.0 CH |
| 6’ | 116.0 C | 116.2 C | 116.3 C | 116.3 C | ||||
| 7’ | 7.60 s | 115.4 CH | 7.61 s | 115.3 CH | 7.52 s | 115.3 CH | 7.54 s | 115.3 CH |
| 8’ | 138.9 C | 139.0 C | 138.3 C | 138.7 C | ||||
| 9’ | 126.2 C | 126.9 C | 125.6 C | 126.3 C | ||||
| 2” | 7.00 s | 125.4 CH | 6.86 s | 126.1 CH | 6.86 s | 123.7 C | 139.3 C | |
| 3” | 108.5 C | 108.5 C | 113.2 C | 106.3 C | ||||
| 4” | 6.75 d (8.5) | 120.6 CH | 6.47 d (8.3) | 120.8 CH | 7.62 d (8.5) | 120.1 CH | 7.38 d (8.6) | 121.6 CH |
| 5” | 6.99 d (8.5) | 123.1 CH | 6.85 d (8.3) | 123.3 CH | 7.15 d (8.5) | 123.2 CH | 7.18 dd (8.4, 1.8) | 123.9 CH |
| 6” | 116.2 C | 116.3 C | 116.1 C | 116.7 C | ||||
| 7” | 7.56 s | 115.3 CH | 7.52 s | 115.2 CH | 7.42 s | 115.2 CH | 7.63 d (1.8) | 115.8 CH |
| 8” | 137.9 C | 138.1 C | 138.3 C | 139.3 C | ||||
| 9” | 128.6 C | 128.7 C | 125.9 C | 125.8 C | ||||
| 2”’ | 6.35 s | 124.4 CH | 6.28 s | 124.4 CH | 6.85 s | 125.6 CH | 7.41 s | 126.2 CH |
| 3”’ | 114.9 C | 115.4 C | 112.2 C | 113.6 C | ||||
| 4”’ | 6.71 d (8.4) | 120.1 CH | 6.59 d (8.6) | 120.4 CH | 7.37 d (8.5) | 120.9 CH | 7.46 d (8.5) | 120.2 CH |
| 5”’ | 6.97 d (8.4) | 123.3 CH | 6.92 d (8.6) | 123.3 CH | 7.02 d (8.5) | 123.1 CH | 7.23 dd (8.5, 1.6) | 123.7 CH |
| 6”’ | 116.0 C | 116.2 C | 115.9 C | 116.6 C | ||||
| 7”’ | 7.38 s | 115.3 CH | 7.38 s | 115.3 CH | 7.40 s | 115.1 CH | 7.61 d (1.6) | 115.9 CH |
| 8”’ | 139.0 C | 139.0 C | 138.8 C | 139.6 C | ||||
| 9”’ | 124.4 C | 124.7 C | 124.8 C | 125.3 C |
a
Not observed in 2D [13C, 1H] HMBC.