Spektraris NMR
2-Debenzoyl-2-tigloylpaclitaxel
Common Name: 2-Debenzoyl-2-tigloylpaclitaxel
Synonyms: Isocephalomannine
CAS Registry Number: 173101-54-7
InChI: InChI=1S/C45H53NO14/c1-9-23(2)40(53)59-38-36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32-24(3)29(21-45(38,55)42(32,6)7)58-41(54)34(50)33(27-16-12-10-13-17-27)46-39(52)28-18-14-11-15-19-28/h9-19,29-31,33-36,38,49-50,55H,20-22H2,1-8H3,(H,46,52)/b23-9+/t29-,30-,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1
InChIKey: InChIKey=YJXDCLDHHJRTGV-WBYYIXQISA-N
Formula: C45H53N1O14
Molecular Weight: 831.9
Exact Mass: 831.3466
NMR Solvent: CDCl3
MHz: 400.0
Calibration: Residual solvent 7.26ppm for proton and 77.0ppm 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 constants missing for ddd at position 6α, d at position 18, and d at NH-3'.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 2 | 5.49 | d | 7.1 |
| 3 | 3.7 | d | 7.1 |
| 5 | 4.94 | dd | 9.5, 2 |
| 6α | 2.54 | ddd | |
| 6β | 1.9 | m | |
| 7 | 4.35 | m | |
| 10 | 6.24 | s | |
| 13 | 6.2 | tq | 8.7, 8.7, 1.5 |
| 14 | 2.24 | m | |
| 16 | 1.09 | s | |
| 17 | 1.22 | s | |
| 18 | 1.76 | d | |
| 19 | 1.64 | s | |
| 20α | 4.38 | d | 7.9 |
| 20β | 4.16 | d | 7.9 |
| 2' | 4.76 | br d | 2.8 |
| 3' | 5.75 | dd | 7, 2.8 |
| OAc-4 | 2.27 | s | |
| OAc-10 | 2.22 | s | |
| NH-3' | 6.96 | d | |
| Ph-3' | 7.19 | m | |
| Tigl-2 H-3 | 7.03 | 7, 1.2 | |
| Tigl-2 2-Me | 1.88 | d | 1.2 |
| Tigl-2 3-Me | 1.87 | d | 7 |
| N-Bz | 7.56 | m |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 78.6 |
| 2 | 71.7 |
| 3 | 45.1 |
| 4 | 80.6 |
| 5 | 84 |
| 6 | 35.1 |
| 7 | 72 |
| 8 | 58.1 |
| 9 | 203.1 |
| 10 | 75.1 |
| 11 | 132.8 |
| 12 | 141.4 |
| 13 | 72.7 |
| 14 | 35 |
| 15 | 42.6 |
| 16 | 21.2 |
| 17 | 26.4 |
| 18 | 14.3 |
| 19 | 9 |
| 20 | 76 |
| 1' | 172.3 |
| 2' | 73.9 |
| 3' | 54.5 |
| Ph (ipso)-3' | 133.3 |
| Ph (ortho)-3' | 126.6 |
| Ph (meta)-3' | 128.3 |
| Ph (para)-3' | 131.6 |
| Tigl-2 C-1 | 168 |
| Tigl-2 C-2 | 127.5 |
| Tigl-2 C-3 | 139.8 |
| Tigl-2 C-4 | 13.6 |
| Tigl-2 C-2 Me | 11.5 |
| OAc-4 | 169.8 |
| OAc-4 | 22 |
| OAc-10 | 170.8 |
| OAc-10 | 20.3 |
| N-Bz | 166.6 |
| N-Bz (ipso) | 137.6 |
| N-Bz (ortho) | 126.6 |
| N-Bz (meta) | 128.6 |
| N-Bz (para) | 127.9 |
