Spektraris NMR
N-Debenzoyl-N-cinnamoyl paclitaxel
Common Name: N-Debenzoyl-N-cinnamoyl paclitaxel
Synonyms: N-Debenzoyl-N-cinnamoyltaxol
CAS Registry Number: 219783-77-4
InChI: InChI=1S/C49H53NO14/c1-27-33(62-45(58)39(55)38(31-18-12-8-13-19-31)50-36(54)23-22-30-16-10-7-11-17-30)25-49(59)43(63-44(57)32-20-14-9-15-21-32)41-47(6,34(53)24-35-48(41,26-60-35)64-29(3)52)42(56)40(61-28(2)51)37(27)46(49,4)5/h7-23,33-35,38-41,43,53,55,59H,24-26H2,1-6H3,(H,50,54)/b23-22+/t33-,34-,35+,38-,39+,40+,41-,43-,47+,48-,49+/m0/s1
InChIKey: InChIKey=SESDEFPIFUOEIX-UFWAFWIVSA-N
Formula: C49H53N1O14
Molecular Weight: 879.94
Exact Mass: 879.3466
NMR Solvent: CDCl3
MHz: 400.0
Calibration: Residual solvent 7.26 ppm for proton and 77.0 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: Aromatic protons not well described. Coupling constants missing for a few signal. See reference for details.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 2 | 5.67 | d | 7.1 |
| 3 | 3.8 | d | 7.1 |
| 5 | 4.93 | dd | 9.5, 2 |
| 6α | 2.48 | m | |
| 6β | 1.85 | m | |
| 7 | 4.39 | m | |
| 10 | 6.28 | s | |
| 13 | 6.23 | tq | 8.7, 8.7, 1.5 |
| 14 | 2.28 | m | |
| 16 | 1.12 | s | |
| 17 | 1.22 | s | |
| 18 | 1.82 | d | |
| 19 | 1.68 | s | |
| 20α | 4.29 | d | 7.9 |
| 20β | 4.19 | d | 7.9 |
| 2' | 4.74 | br d | 2.8 |
| 3' | 5.7 | dd | 7, 2.8 |
| OAc-4 | 2.38 | s | |
| OAc-10 | 2.2 | s | |
| NH-3' | 6.46 | d | |
| Ph-3' | 7.24 | m | |
| Bz-2 | 8.1 | ||
| Bz-2 | 7.65 | ||
| Bz-2 | 7.25 | ||
| N-Cinn H-2 | 6.45 | d | 15.6 |
| N-Cinn H-3 | 5.7 | d | 15.6 |
| 3-Ph | 7.67 |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 78.3 |
| 2 | 74.5 |
| 3 | 45.3 |
| 4 | 80.7 |
| 5 | 84 |
| 6 | 35.2 |
| 7 | 73.1 |
| 8 | 57.9 |
| 9 | 203.4 |
| 10 | 75.2 |
| 11 | 134.1 |
| 12 | 141.6 |
| 13 | 71.5 |
| 14 | 35.2 |
| 15 | 42.7 |
| 16 | 21.4 |
| 17 | 26.3 |
| 18 | 14.4 |
| 19 | 9.1 |
| 20 | 76 |
| 1' | 172.4 |
| 2' | 71.5 |
| 3' | 54.8 |
| Ph (ipso)-3' | 128.9 |
| Ph (ortho)-3' | 129.8 |
| Ph (meta)-3' | 128.3 |
| Ph (para)-3' | 133.3 |
| Bz-2 | 166.4 |
| Bz-2 (ipso) | 128.9 |
| Bz-2 (ortho) | 129.8 |
| Bz-2 (meta) | 128.3 |
| Bz-2 (para) | 133.3 |
| OAc-4 | 170.1 |
| OAc-4 | 22.1 |
| OAc-10 | 170.8 |
| OAc-10 | 20.3 |
| N-Cinn | 165.7 |
| N-Cinn C-2 | 119.5 |
| N-Cinn C-3 | 141.7 |
| N-Cinn (ipso) | 137.8 |
| N-Cinn (ortho) | 127.4 |
| N-Cinn (meta) | 128.4 |
| N-Cinn (para) | 127.7 |
