Table 1.
1H and 13C chemical shifts of 12α-DHADD, 12β-DHADD, 12α-20S-DHOPDCA, and 12α-20R-DHOPDCAa
| Atom no. | 12α-DHADD (XVI) in MeOD |
12β-DHADD (XVIII) in D2O |
12α-20S-DHOPDCA (XI) in MeOD |
12α-20R-DHOPDCA in MeOD |
||||
|---|---|---|---|---|---|---|---|---|
| δC (ppm) | δH (ppm), 2,3,4JHHb | δC (ppm) | δH (ppm), 2,3,4JHH | δC (ppm) | δH (ppm), 2,3,4JHH | δC (ppm) | δH (ppm), 2,3,4JHH | |
| 1 | 157.6 | 7.29, d, 10.4 Hz | 159.5 | 7.38, d, 10.4 Hz | 157.6 | 7.29, m | 157.6 | 7.29, d, 10.6 Hz |
| 2 | 126.0 | 2.26, dd, 10.4/1.7 Hz | 125.7 | 6.28, dd, 10.4/2.0 Hz | 125.9 | 6.24, d, 9.8 Hz | 125.9 | 6.24, d, 10.6 Hz |
| 3 | 186.9 | —c | 188.5 | — | — | — | — | — |
| 4 | 125.8 | 6.15, td, 3.0/1.7 Hz | 125.3 | 6.16, t, 1.8 Hz | 125.3 | 6.12, s | 125.3 | 6.12, s |
| 5 | 168.3 | — | 170.1 | — | 168.5 | — | 168.5 | — |
| 6 | 40.2 | 2.58, dd, 14.2/3.1 Hz | 40.0 | 2.54, dd, 14.3/3.2 Hz | 40.4 | 2.52, dd, 13.7/2.0 Hz | 40.4 | 2.52, dd, 13.5/2.8 Hz |
| 2.87, m | 2.83, ddd, 14.3/3.2/1.8 Hz | 2.80, m, 13.7 Hz | 2.80, m, 13.5 Hz | |||||
| 7 | 67.7 | 4.20, q, 2.7 Hz | 67.8 | 4.22, q, 3.2 Hz | 68.8 | 4.05, m | 68.7 | 4.05, m |
| 8 | 38.8 | 2.08, m | 37.3 | 1.99, m | 39.7 | 1.78, m | 39.5 | 1.80, m |
| 9 | 39.0 | 2.05, m | 42.6 | 1.54, m | 38.5 | 1.97, m | 38.1 | 2.00, m |
| 10 | 43.3 | — | 43.8 | — | 43.2 | — | 43.4 | — |
| 11 | 29.2 | 1.94, m | 29.9 | 1.69axial, td, 12.9/11.2 Hz | — | — | — | — |
| 2.01, m | 1.95equatorial, m | — | — | — | — | |||
| 12 | 68.2 | 4.09, m | 70.5 | 3.71, dd, 11.2/4.7 Hz | — | — | — | — |
| 13 | 52.3 | — | 51.5 | — | 53.6 | — | 50.2 | — |
| 14 | 37.8 | 2.44, m | 43.2 | 1.53, m | 38.6 | 1.95, m | 41.3 | 1.98, m |
| 15 | 20.3 | 1.68, m | 20.3 | 1.77, tt, 12.8/9.2 Hz | 24.6 | 1.36, m | 24.8 | 1.36, m |
| 2.17, m | 2.00, m | 1.62, m | 1.62, m | |||||
| 16 | 36.2 | 2.13, m | 35.4 | 2.13, dt, 20.2/9.2 Hz | 28.5 | 1.36, m | 28.7 | 1.35, m |
| 2.44, m | 2.49, dd, 20.2/9.0 Hz | 1.63, m | 1.63, m | |||||
| 17 | 220.1 | — | 224.5 | — | 42.7 | 2.31, m | 41.9 | 2.27, t, 7.4 Hz |
| 18 | 13.1 | 0.95, s | 7.2 | 0.97, s | 7.2 | 0.90, m | 9.1 | 1.05, m |
| 19 | 17.3 | 1.31, s | 17.4 | 1.25, s | 17.2 | 1.27, s | 17.2 | 1.28, s |
| 20 | 48.4 | 2.31, m | 48.9 | 2.35, m | ||||
| 21 | 12.3 | 1.07, d, 5.3 Hz | 11.2 | 1.19, d, 7.0 Hz | ||||
| 22 | 206.8 | 9.56, d, 4.8 Hz | 205.3 | 9.56, d, 2.9 Hz | ||||
a
12α-DHADD, XVI in Fig. 1 and P4 in Fig. 4 and 5; 12β-DHADD, XVIII in Fig. 1; 12α-20S-DHOPDCA, XI in Fig. 1 and P5 in Fig. 4; 12α-20R-DHOPDCA, P7.
b
s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; dd, doublet of a doublet; td, triplet of a doublet; tt, triplet of a triplet; ddd, doublet of a doublet of a doublet.
c
—, no proton at given position, or proton resonance could not be assigned.