Spektraris NMR
Taxol C
Common Name: Taxol C
Synonyms: Taxuyunnanine A
CAS Registry Number: 153415-45-3
InChI: InChI=1S/C46H57NO14/c1-8-9-12-21-33(51)47-35(28-17-13-10-14-18-28)36(52)42(55)59-30-23-46(56)40(60-41(54)29-19-15-11-16-20-29)38-44(7,31(50)22-32-45(38,24-57-32)61-27(4)49)39(53)37(58-26(3)48)34(25(30)2)43(46,5)6/h10-11,13-20,30-32,35-38,40,50,52,56H,8-9,12,21-24H2,1-7H3,(H,47,51)/t30-,31-,32+,35-,36+,37+,38-,40-,44+,45-,46+/m0/s1
InChIKey: InChIKey=BEHTXUBGUDGCNQ-IEAAAIHOSA-N
Formula: C46H57N1O14
Molecular Weight: 847.94
Exact Mass: 847.3779
NMR Solvent: CDCl3
MHz: 300.0
Calibration: TMS
NMR references: Barboni, L., Gariboldi, P., Torregiani, E., Appendino, G., Gabetta, B., and Bombardelli, E. (1994). Taxol analogues from the roots of Taxus x media. Phytochemistry 36, 987–990.
Species: Taxus
Notes: Multiplets for protons at 14α,β, 4", and 5" cover range of 0.8 ppm. In our table we report the center ppm value of each multiplet. Symbols ' refer to proton and carbon on phenylisoserine side chain while " refers to protons and carbon on alkyl side chain. See literature for further details.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 2 | 5.66 | d | 7 |
| 3 | 3.78 | d | 7 |
| 5 | 4.93 | dd | 9.4, 2 |
| 6α | 2.54 | ddd | 15.5, 9.4, 6.6 |
| 6β | 1.84 | ddd | 15.5, 10.9, 2 |
| 7 | 4.39 | ddd | 10.9, 6.6, 4.1 |
| 10 | 6.28 | s | |
| 13 | 6.23 | br t | 9 |
| 14α | 2.28 | m | |
| 14β | 2.28 | m | |
| 16 | 1.26 | s | |
| 17 | 1.14 | s | |
| 18 | 1.81 | d | 1.2 |
| 19 | 1.67 | s | |
| 20α | 4.28 | d | 8.6 |
| 20β | 4.17 | d | 8.6 |
| 2' | 4.65 | dd | 4.9, 2.5 |
| 3' | 5.56 | dd | 8.9, 2.5 |
| 2" | 2.18 | t | 7.3 |
| 3" | 1.56 | m | |
| 4" | 1.24 | m | |
| 5" | 1.24 | m | |
| 6" | 0.83 | t | 6.7 |
| Bnz 2-6 | 8.1 | d | 7.8 |
| Bnz 3-5 | 7.5 | t | 7.8 |
| Bnz 4 | 7.61 | t | 7.8 |
| Ph | 7.38 | m | |
| MeCO | 2.29 | s | |
| NH | 6.25 | d | 8.9 |
| 7-OH | 2.49 | d | 4.1 |
| 1-OH | 1.84 | s | |
| 2'-OH | 3.55 | d | 4.9 |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 79 |
| 2 | 74.9 |
| 3 | 45.6 |
| 4 | 81.1 |
| 5 | 84.4 |
| 6 | 35.6 |
| 7 | 72.2 |
| 8 | 58.6 |
| 9 | 203.6 |
| 10 | 75.6 |
| 11 | 133.1 |
| 12 | 142.1 |
| 13 | 72.3 |
| 14 | 35.6 |
| 15 | 43.2 |
| 16 | 26.8 |
| 17 | 21.9 |
| 18 | 14.8 |
| 19 | 9.5 |
| 20 | 76.5 |
| 1' | 172.8 |
| 2' | 73.2 |
| 3' | 54.5 |
| 1" | 173 |
| 2" | 36.6 |
| 3" | 25.3 |
| 4" | 31.3 |
| 5" | 22.3 |
| 6" | 13.9 |
| Bnz 1 | 129.1 |
| Bnz 2-6 | 130.2 |
| Bnz 3-5 | 128.7 |
| Bnz 4 | 133.7 |
| Ph 1 | 138.1 |
| Ph 2-6 | 126.9 |
| Ph 3-5 | 128.9 |
| Ph 4 | 128.2 |
| MeCO | 21.7 |
| MeCO | 170.7 |
| BnzCO | 167 |
