Table 3.
1H and 13C NMR Data (δ) for CBGA Esters 7 and 11 and CBNA Ester 8 in CDCl3 (J in Hz)
| no. | δH of CBGAa | δC of CBGAb | (δH of 7a | (δH of 11a | δC of 11b | no. | δH of CBNAa | δC of CBNAb | δH of 8a | δC of 8b |
|---|---|---|---|---|---|---|---|---|---|---|
| 1 | 3.44 (d, J = 7.0) | 22.7 | 3.44 (d, J = 7.0) | 3.44 (d, J = 7.0) | 22.7 | 1 | 163.7 | 163.9 | ||
| 2 | 5.28 (t, J = 7.0) | 121.5 | 5.28 (t, J = 7.0) | 5.28 (t, J = 7.0) | 121.6 | 2 | 104.2 | 104.9 | ||
| 3 | 139.3 | 139.5 | 3 | 149.2 | 149.5 | |||||
| 4 | 2.21 m | 40.0 | 2.19 m | 2.21 m | 40.0 | 4 | 6.44 s | 113.2 | 6.44 s | 113.2 |
| 5 | 2.11 m | 26.6 | 2.11 m | 2.11 m | 26.6 | 5 | 159.5 | 159.2 | ||
| 6 | 5.06 (t, J = 6.4) | 124.0 | 5.07 (t, J = 7.0) | 5.07 (t, J = 6.4) | 124.0 | 6 | 78.8 | 78.7 | ||
| 7 | 130.2 | 130.2 | 6a | 136.0 | 136.0 | |||||
| 8 | 1.58 s | 17.9 | 1.58 s | 1.58 s | 17.9 | 7 | 7.14 (d, J = 7.8) | 122.5 | 7.14 (d, J = 7.8) | 122.5 |
| 9 | 1.68 s | 25.9 | 1.69 s | 1.68 s | 25.9 | 8 | 7.11 (d, J = 7.8) | 128.2 | 7.09 (d, J = 7.8) | 128.2 |
| 10 | 1.83 s | 16.4 | 1.82 s | 1.83 s | 16.4 | 9 | 137.2 | 137.2 | ||
| 1′ | 163.0 | 163.0 | 10 | 8.46 s | 127.3 | 8.46 s | 127.3 | |||
| 2′ | 104.0 | 104.0 | 10a | 127.3 | 127.3 | |||||
| 3′ | 147.0 | 147.0 | 10b | 109.2 | 109.2 | |||||
| 4′ | 6.23 s | 111.4 | 6.22 s | 6.23 s | 111.4 | 11 | 2.38 s | 21.8 | 2.40 s | 21.8 |
| 5′ | 162.3 | 162.3 | 12 | 1.62 s | 27.6 | 1.63 s | 27.6 | |||
| 6′ | 110.0 | 110.0 | 13 | 1.62 s | 27.6 | 1.63 s | 27.6 | |||
| 1″ | 2.71 (t, J = 7.2) | 36.8 | 2.72 (t, J = 7.2) | 2.71 (t, J = 7.2) | 37.0 | 1′ | 2.94 m | 37.0 | 2.97 m | 37.1 |
| 2″ | 1.60 m | 31.7 | 1.60 m | 1.60 m | 31.7 | 2′ | 1.66 m | 31.4 | 1.66 m | 31.4 |
| 3″ | 1.36 m | 32.2 | 1.36 m | 1.36 m | 32.2 | 3′ | 1.26 m | 32.2 | 1.26 m | 32.2 |
| 4″ | 1.36 m | 22.7 | 1.36 m | 1.36 m | 22.7 | 4′ | 1.26 m | 22.8 | 1.26 m | 22.8 |
| 5″ | 0.88 (t, J = 7.2) | 14.3 | 0.88 (t, J = 7.2) | 0.88 (t, J = 7.2) | 14.3 | 5′ | 0.91 (t, J = 6.9) | 14.3 | 0.91 (t, J = 6.9) | 14.3 |
| 1‴ | 1.61, 1.42 m | 85.0 | 1″ | 89.0 | ||||||
| 2‴ | 1.69 m | 1.58 m | 35.4 | 2″ | 1.93 m | 34.7 | ||||
| 3‴ | 1.99, 195 m | 1.91 m | 18.7 | 3″ | 5.31 (t, J = 11.8) | 118.5 | ||||
| 4‴ | 2.01 m | 37.0 | 4″ | 134.2 | ||||||
| 5‴ | 1.28 m | 44.3 | 5″ | 1.93 m | 27.3 | |||||
| 6‴ | 1.98, 1.82 m | 5.55 (d, J = 11.8) | 125.0 | 6″ | 1.26 m | 31.0 | ||||
| 7‴ | 1.59 | 134.6 | 7″ | 3.02 sep | 37.2 | |||||
| 8‴ | 1.27, 1.48 m | 2.01 m | 31.3 | 8″ | 1.69 s | 23.5 | ||||
| 9‴ | 1.38, 1.14 | 1.32 m | 21.7 | 9″ | 0.95 (d, J = 6.4) | 17.1 | ||||
| 10‴ | 2.16 m | 54.3 | 10″ | 0.95 (d, J = 6.4) | 18.1 | |||||
| 11‴ | 1.90 m | 26.6 | 11″ | |||||||
| 12‴ | 1.28 s | 0.94 (d, J = 6.0) | 21.9 | 12″ | ||||||
| 13‴ | 1.28 s | 0.81 (d, J = 7.0) | 15.5 | 13″ | ||||||
| 14‴ | 1.63 s | 1.28 s | 28.1 | 14″ | ||||||
| 15‴ | 1.06 s | 1.69 s | 23.8 | 15″ | ||||||
| OH | 11.60 s | 12.52 s | 12.25 s | OH | 12.78 s | 12.85 s | ||||
| COOH | 176.2 | 171.3 | COOH | 176.2 | 171.9 |
a
400 MHz.
b
100 MHz.