Spektraris NMR
Taxol
Common Name: Taxol
Synonyms: Paclitaxel
CAS Registry Number: 33069-62-4
InChI: InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
InChIKey: InChIKey=RCINICONZNJXQF-MZXODVADSA-N
Formula: C47H51N1O14
Molecular Weight: 853.91
Exact Mass: 853.331
NMR Solvent: CDCl3
MHz: 500.0
Calibration: TMS proton nmr. CDCl3 in 13C NMR set to 77.00 ppm relative to TMS
NMR references: Chmurny, G.N., Hilton, B.D., Brobst, S., Look, S.A., Witherup, K.M., and Beutler, J.A. (1992). 1H- and 13C-nmr Assignments for Taxol, 7-epi-Taxol, and Cephalomannine. J. Nat. Prod. 55, 414–423.
Species: Taxus
Notes: In order to distinguish aromatic protons (abbreviated Ph in table standing for phenyl) on different rings authors named the benzoyl substitutient at position 2 ring 1, the aromatic ring connected to 3' on the phenylisoserine side chain named ring 2, and the benzoyl ring connected to N ring 3. Also note that protons at position H-7, OH-7, H-2', OH-2' J values differ depending on exhange of hydroxls. We use data from literature corresonpding to rapid exhange of hydroxyl protons. See literature for details
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 1-OH | 1.98 | br s | |
| 2 | 5.67 | d | 7.1 |
| 3 | 3.79 | dd | 7, 1 |
| 4-OAc | 2.38 | s | |
| 5 | 4.94 | dddd | 9.6, 2.3, 0.9, 0.8 |
| 6a | 2.54 | ddd | 14.8, 9.7, 6.7 |
| 6b | 1.88 | ddd | 14.7, 11, 2.3 |
| 7 | 4.4 | dd | 10.9, 6.7 |
| 7-OH | 2.48 | br s | |
| 10 | 6.27 | s | |
| 10-OAc | 2.23 | s | |
| 13 | 6.23 | q | 9, 1.5 |
| 14a | 2.35 | dd | 15.4, 9 |
| 14b | 2.28 | ddd | 15.3, 9, 0.6 |
| 16 | 1.14 | s | |
| 17 | 1.24 | s | |
| 18 | 1.79 | d | 1.5 |
| 19 | 1.68 | s | |
| 20a | 4.3 | ddd | 8.4, 1.1, 0.8 |
| 20b | 4.19 | dd | 8.5, 1 |
| 2' | 4.78 | d | 2.7 |
| 2'-OH | 3.61 | br s | |
| 3' | 5.78 | dd | 8.9, 2.8 |
| 3'-NH | 7.01 | d | 8.9 |
| o-Ph 1 | 8.13 | dd | 8.4, 1.3 |
| m-Ph 1 | 7.51 | m | |
| p-Ph 1 | 7.61 | tt | 7.4, 1.4 |
| o-Ph 2 | 7.48 | m | |
| m-Ph 2 | 7.42 | m | |
| p-Ph 2 | 7.35 | tt | 7.3, 1.6 |
| o-Ph 3 | 7.74 | dd | 8.3, 1.2 |
| m-Ph 3 | 7.4 | m | |
| p-Ph 3 | 7.49 | m |
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 | 75.5 |
| 11 | 133.2 |
| 12 | 142 |
| 13 | 72.3 |
| 14 | 35.7 |
| 15 | 43.2 |
| 16 | 21.8 |
| 17 | 26.9 |
| 18 | 14.8 |
| 19 | 9.5 |
| 20 | 76.5 |
| 1' | 172.7 |
| 2' | 73.2 |
| 3' | 55 |
| 4-OAc C=O | 170.4 |
| 4-OAc methyl | 22.6 |
| 10-OAc C=O | 171.2 |
| 10-OAc methyl | 20.8 |
| Ph1 C=O | 129.1 |
| q-Ph1 | 129.1 |
| o-Ph1 | 130.2 |
| m-Ph1 | 128.71 |
| p-Ph1 | 133.7 |
| q-Ph2 | 133.6 |
| o-Ph2 | 127.03 |
| m-Ph2 | 128.68 |
| p-Ph2 | 131.9 |
| Ph3 C=O | 167.02 |
| q-Ph3 | 138 |
| o-Ph 3 | 127.04 |
| m-Ph 3 | 129 |
| p-Ph 3 | 128.3 |
