Spektraris NMR
1-Deoxypaclitaxel
Common Name: 1-Deoxypaclitaxel
Synonyms: 1-Deoxytaxol
CAS Registry Number: 198990-70-4
InChI: InChI=1S/C47H51NO13/c1-25-32(59-44(56)37(52)36(28-16-10-7-11-17-28)48-42(54)29-18-12-8-13-19-29)22-31-38(60-43(55)30-20-14-9-15-21-30)40-46(6,33(51)23-34-47(40,24-57-34)61-27(3)50)41(53)39(58-26(2)49)35(25)45(31,4)5/h7-21,31-34,36-40,51-52H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33-,34+,36-,37+,38+,39+,40-,46+,47-/m0/s1
InChIKey: InChIKey=NMFSXFNXTSCWAD-IKOAQKMTSA-N
Formula: C47H51N1O13
Molecular Weight: 837.91
Exact Mass: 837.336
NMR Solvent: CDCl3
MHz: 500.0
Calibration: Not mentioned in reference.
NMR references: Shi, Q.-W., Zhao, Y.-M., Si, X.-T., Li, Z.-P., Yamada, T., and Kiyota, H. (2006). 1-Deoxypaclitaxel and abeo-Taxoids from the Seeds of Taxus mairei. J. Nat. Prod. 69, 280–283.
Species: Taxus
Notes: Coupling constants missing on a few aromatic triplets (t) due to overlap. See reference for details. 1' carbon assignment missing.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 1 | 2.14 | m | |
| 2 | 5.65 | dd | 6.9, 2.9 |
| 3 | 3.63 | d | 6.9 |
| 5 | 4.99 | d | 10.2 |
| 6α | 2.56 | m | |
| 6β | 1.88 | m | |
| 7 | 4.41 | m | |
| OH-7 | 2.41 | br | |
| 10 | 6.24 | s | |
| 13 | 6.05 | t | 8.6 |
| 14α | 1.71 | m | |
| 14β | 2.51 | m | |
| 16 | 1.17 | s | |
| 17 | 1.22 | s | |
| 18 | 1.8 | s | |
| 19 | 1.66 | s | |
| 20a | 4.38 | d | 8.3 |
| 20b | 4.15 | d | 8.3 |
| OAc-4 | 2.38 | s | |
| OAc-10 | 2.22 | s | |
| OBz-2 o | 8.09 | d | 7.4 |
| OBz-2 m | 7.49 | t | |
| OBz-2 p | 7.6 | t | 7.4 |
| 2' | 4.78 | dd | 4.5, 2.4 |
| OH-2' | 3.48 | br d | 4.5 |
| 3' | 5.77 | dd | 9, 2.4 |
| Ph-3' | 7.42 | m | |
| NH | 6.96 | d | 9 |
| NBz-3' o | 7.7 | d | 7.6 |
| NBz-3' m | 7.41 | t | |
| NBz-3' p | 7.47 | t |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 45.4 |
| 2 | 72.1 |
| 3 | 43.3 |
| 4 | 81.1 |
| 5 | 84.2 |
| 6 | 35.6 |
| 7 | 72 |
| 8 | 58.9 |
| 9 | 204 |
| 10 | 75.6 |
| 11 | 132.9 |
| 12 | 140.2 |
| 13 | 72.1 |
| 14 | 26.6 |
| 15 | 38.3 |
| 16 | 30.2 |
| 17 | 26 |
| 18 | 14.8 |
| 19 | 9.5 |
| 20 | 76.6 |
| OAc-4 | 22.5 |
| OAc-4 | 170.1 |
| OAc-10 | 20.8 |
| OAc-10 | 171.2 |
| OBz-2 ipso | 165 |
| OBz-2 o | 129.8 |
| OBz-2 m | 128.5 |
| OBz-2 p | 133.5 |
| 2' | 73 |
| 3' | 54.7 |
| Ph-3' | 128.5 |
| Ph-3' | 126.9 |
| NBz-3' C=O | 166.9 |
| NBz-3' o | 126.9 |
| NBz-3' m | 128.8 |
| NBz-3' p | 131.7 |
