NMR results for M1 and the synthetic N-glucuronide 2 and the S-glucuronide 3 of tanaproget
Position | δ13C | δ1H, 1H Multiplicitya/J (in Hz)a | 1H-13C HMBC (1H to 13C) M1 | ||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| 2 | 3 | M1 | 2 | 3 | M1 | ||||||
| 2 | 82.1 | 81.5 | 82.4 | ||||||||
| 3 | 132.0 | 131.2 | 127.4 | ||||||||
| 4 | 131.5 | 137.8 | 138.7 | ||||||||
| 6 | 188.0 | 161.3 | 161.6 | ||||||||
| 7 | 123.1 | 123.4 | 125.0 | 7.50, d/1.7 | 7.40, d/2.0 | 7.40, s | C-2, C-4, C-9, C-14 | ||||
| 8 | 127.7 | 128.3 | 132.6 | ||||||||
| 9 | 128.1 | 128.9 | 130.0 | 7.57, dd/1.7, 8.5 | 7.41, dd/2.0, 7.9 | 7.39, dd/∼9, 2.4 | C-4, C-7, C-14 | ||||
| 10 | 118.1 | 123.4 | 124.0 | 7.80, d/8.5 | 7.11, d/7.9 | 7.09, d/8.0 | C-3, C-8, C-9 | ||||
| 11 | 25.3b | 27.2 | 28.2 | 1.63, s | 1.70, s | 1.62, s | C-2, C-3 | ||||
| 12 | 25.5b | 27.8 | 28.2 | 1.83, s | 1.59, s | 1.62, s | C-2, C-3 | ||||
| 14 | 138.6 | 139.5 | 140.7 | ||||||||
| 16 | 104.8 | 104.7 | 105.8 | ||||||||
| 17 | 119.2 | 119.6 | 120.3 | 7.05, d/4 | 7.03, d/4 | 7.05, d/3.6 | C-14, C-16, C-18 | ||||
| 18 | 109.8 | 109.7 | 110.5 | 6.43, d/4 | 6.38, d/4 | 6.36, d/4.0 | C-14, C-16, C-17 | ||||
| 19 | 33.6 | 33.8 | 34.9 | 3.75, s | 3.73, s | 3.69, s | C-14, C-16 | ||||
| 20 | 113.7 | 114.2 | |||||||||
| 1′ | 90.2 | 85.0 | 85.6 | 6.31, d/9.5 | 5.11, d/10.2 | 5.10, d/10.3 | C-6 | ||||
| 2′ | 68.6 | 72.1 | 70.4 | 3.70, m | 3.11, t/9.4 | 3.14, m | |||||
| 3′ | 78.0 | 78.3 | 71.3c | 3.31, m | 3.22, t/9.3 | 3.24c, t/8.7 | |||||
| 4′ | 71.9 | 71.7 | 70.6c | 3.30, m | 3.11, t/9.4 | 3.29c | |||||
| 5′ | 76.8 | 78.4 | 74.6 | 3.39, m | 3.31, d/10.0 | 3.37, d/10.0 | COOH | ||||
| COOH | 171.2 | 171.3 | 172.7 |
|
|
| 3.29c | ||||
↵ a 1H multiplicities are reported as s = singlet, d = doublet, dd = doublet of doublet, and m = multiplet. 1H - 1H J coupling constants are stated in Hz.
↵ b 13C signals δ25.3 and δ 25.5 could not be individually assigned to C-11 vs. C-12 for 2.
↵ c Unambiguous assignments to H3′ vs. H4′ could not be made for M1. δ3.24/71.3 (t, J = 8.7 Hz) is observed in gHSQC, 1D, and 2D total correlation spectroscopy spectra, and δ3.29/70.6 is observed in an HMBC spectrum.