Spektraris NMR
N-Debenzoyl-N-α-methylbutyrylpaclitaxel
Common Name: N-Debenzoyl-N-α-methylbutyrylpaclitaxel
Synonyms: N-debenzoyl-N-(2-methylbutyryl)taxol
CAS Registry Number: 159001-25-9
InChI: InChI=1S/C45H55NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32(24(29)3)42(45,6)7/h10-19,23,29-31,33-36,38,49-50,55H,9,20-22H2,1-8H3,(H,46,52)
InChIKey: InChIKey=OKEKLOJNCOIPIT-UHFFFAOYSA-N
Formula: C45H55N1O14
Molecular Weight: 833.92
Exact Mass: 833.3623
NMR Solvent: CDCl3
MHz: 400.0
Calibration: Residual solvent 7.26 ppm for proton and 77.0 ppm for carbon.
NMR references: Gabetta, B., Fuzzati, N., Orsini, P., Peterlongo, F., Appendino, G., and Vander Velde, D.G. (1999). Paclitaxel Analogues from Taxus × media cv. Hicksii. J. Nat. Prod. 62, 219–223.
Species: Taxus
Notes: Coupling constant missing from NH-3' doublet.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 2 | 5.69 | d | 7.2 |
| 3 | 3.79 | d | 7.2 |
| 5 | 4.95 | dd | 9.5, 1.8 |
| 6α | 2.55 | m | |
| 6β | 1.88 | m | |
| 7 | 4.39 | m | |
| 10 | 6.31 | s | |
| 13 | 6.17 | tq | 9.1, 9.1, 1 |
| 14 | 2.29 | m | |
| 16 | 1.14 | s | |
| 17 | 1.23 | s | |
| 18 | 1.88 | d | |
| 19 | 1.68 | s | |
| 20α | 4.29 | d | 8 |
| 20β | 4.21 | d | 8 |
| 2' | 4.65 | br d | 2.9 |
| 3' | 5.59 | dd | 8.9, 2.9 |
| OAc-4 | 2.37 | s | |
| OAc-10 | 2.23 | s | |
| NH-3' | 7.06 | d | |
| Ph-3' | 7.3 | m | |
| Bz-2 | 8.11 | ||
| Bz-2 | 7.61 | ||
| Bz-2 | 7.51 | ||
| N-α-MeBu H-2 | 2.2 | qd | 6.7, 1.4 |
| N-α-MeBu H-3a | 1.64 | m | |
| N-α-MeBu H-3b | 1.39 | ddq | 13.3, 7.5, 1.4 |
| N-α-MeBu H-4 | 0.87 | t | 7.4 |
| N-α-MeBu 2-Me | 1.1 | d | 6.7 |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 78.6 |
| 2 | 74.9 |
| 3 | 45.5 |
| 4 | 81 |
| 5 | 84.3 |
| 6 | 35.6 |
| 7 | 71.9 |
| 8 | 58.4 |
| 9 | 203.7 |
| 10 | 75.6 |
| 11 | 138.5 |
| 12 | 142.1 |
| 13 | 72 |
| 14 | 35.5 |
| 15 | 43.2 |
| 16 | 22.5 |
| 17 | 26.6 |
| 18 | 14 |
| 19 | 9.5 |
| 20 | 76.4 |
| 1' | 172.8 |
| 2' | 73.4 |
| 3' | 54.4 |
| Ph (ipso)-3' | 133 |
| Ph (ortho)-3' | 126.8 |
| Ph (meta)-3' | 128.6 |
| Ph (para)-3' | 127.7 |
| Bz-2 | 166.6 |
| Bz-2 (ipso) | 129.3 |
| Bz-2 (ortho) | 130.1 |
| Bz-2 (meta) | 128.7 |
| Bz-2 (para) | 133.4 |
| OAc-4 | 170.1 |
| OAc-4 | 22.6 |
| OAc-10 | 171 |
| OAc-10 | 26.8 |
| N-MeBu C-1 | 176.1 |
| N-MeBu C-2 | 42.9 |
| N-MeBu C-3 | 27 |
| N-MeBu C-4 | 14 |
| N-MeBu 2-Me | 17.4 |
