Spektraris NMR
5α-O-(3'-dimethylamino-3'-phenylpropionyl) taxinine M
Common Name: 5α-O-(3'-dimethylamino-3'-phenylpropionyl) taxinine M
Synonyms: 5α-[(R)-3'-Dimethylamino-3'-phenylpropanoyloxy]taxinine M
CAS Registry Number: 358331-50-7
InChI: InChI=1S/C46H55NO15/c1-25-34(62-37(53)21-33(47(8)9)30-16-12-10-13-17-30)22-36(58-26(2)48)45(24-56-42(54)31-18-14-11-15-19-31)38(25)39(59-27(3)49)32-20-35(52)44(7)46(55,43(32,6)23-57-44)41(61-29(5)51)40(45)60-28(4)50/h10-19,32-34,36,38-41,55H,1,20-24H2,2-9H3/t32-,33+,34-,36?,38-,39+,40-,41-,43-,44+,45?,46-/m0/s1
InChIKey: InChIKey=OTDMUTOTRRFOKJ-JISOTWSESA-N
Formula: C46H55N1O15
Molecular Weight: 861.93
Exact Mass: 861.3572
NMR Solvent: CDCl3
MHz: 500.0
Calibration: Not mentioned.
NMR references: Prasain, J.K., Stefanowicz, P., Kiyota, T., Habeichi, F., and Konishi, Y. (2001). Taxines from the needles of Taxus wallichiana. Phytochemistry 58, 1167–1170.
Species: Taxus
Notes: Relative stereochemistry not reported for protons at position 6 and 14. Carbon assignment missing for position 1'.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 1 | 2.48 | m | |
| 2 | 6.11 | br d | 10.2 |
| 3 | 3.42 | d | 10.2 |
| 5 | 5.23 | br s | |
| 6 | 2 | m | |
| 6 | 1.55 | m | |
| 7 | 5.34 | br d | 6.2 |
| 9 | 5.31 | d | 3 |
| 10 | 5.29 | d | 3 |
| 11 | 4.15 | br s | |
| 14 | 3.1 | dd | 19.2, 11.5 |
| 14 | 2.65 | d | 19.2 |
| 16 | 1.26 | ||
| 17 | 4.1 | d | 7.9 |
| 17 | 3.65 | d | 8 |
| 18 | 1.15 | s | |
| 19 | 5.19 | d | 12.2 |
| 19 | 4.37 | d | 12.2 |
| 20 | 5.49 | s | |
| 20 | 4.75 | s | |
| N(Me)2 | 2.76 | s | |
| N(Me)2 | 2.88 | s | |
| 19-OBz (ortho) | 8.12 | d | 7.9 |
| 19-OBz (meta) | 7.48 | m | |
| 19-OBz (para) | 7.58 | m | |
| 2' | 3.78 | m | |
| 3' | 4.95 | m | |
| 3'-Ph (ortho) | 7.48 | m | |
| 3'-Ph (meta) | 7.48 | m | |
| 3'-Ph (para) | 7.48 | m | |
| Ac | 1.97 | s | |
| Ac | 2.11 | s | |
| Ac | 1.97 | s | |
| Ac | 2.06 | s |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 48.1 |
| 2 | 69.5 |
| 3 | 40 |
| 4 | 140 |
| 5 | 76 |
| 6 | 40 |
| 7 | 64 |
| 8 | 49.7 |
| 9 | 70.4 |
| 10 | 64 |
| 11 | 80.2 |
| 12 | 91.4 |
| 13 | 205.7 |
| 14 | 34.5 |
| 15 | 49.7 |
| 16 | 15.4 |
| 17 | 82.2 |
| 18 | 11.9 |
| 19 | 60.8 |
| 20 | 116.7 |
| N(Me)2 | 38.8 |
| N(Me)2 | 42.3 |
| 19-OCOC6H5 | 167.5 |
| 19-OBz (ipso) | 130.1 |
| 19-OBz (ortho) | 130.1 |
| 19-OBz (meta) | 128.6 |
| 19-OBz (para) | 133.7 |
| 2' | 35.9 |
| 3' | 65.9 |
| 3'-Ph (ipso) | 141 |
| 3'-Ph (ortho) | 130.1 |
| 3'-Ph (meta) | 128.6 |
| 3'-Ph (para) | 128.6 |
| Ac | 168 |
| Ac | 168 |
| Ac | 168 |
| Ac | 172.2 |
| Ac | 21.2 |
| Ac | 21.2 |
| Ac | 20.5 |
| Ac | 20.5 |
