Spektraris NMR
7-epi-10-Deacetyltaxol
Common Name: 7-epi-10-Deacetyltaxol
Synonyms: 10-Deacetyl-7-epi-taxol
CAS Registry Number: 78454-17-8
InChI: InChI=1S/C45H49NO13/c1-24-29(57-41(54)35(50)33(26-15-9-6-10-16-26)46-39(52)27-17-11-7-12-18-27)22-45(55)38(58-40(53)28-19-13-8-14-20-28)36-43(5,37(51)34(49)32(24)42(45,3)4)30(48)21-31-44(36,23-56-31)59-25(2)47/h6-20,29-31,33-36,38,48-50,55H,21-23H2,1-5H3,(H,46,52)/t29-,30+,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1
InChIKey: InChIKey=TYLVGQKNNUHXIP-DIYBZAJCSA-N
Formula: C45H49N1O13
Molecular Weight: 811.87
Exact Mass: 811.3204
NMR Solvent: CDCl3
MHz: 500.0
Calibration: TMS
NMR references: McLaughlin, J.L., Miller, R.W., Powell, R.G., and Smith, C.R. (1981). 19-Hydroxybaccatin III, 10-Deacetylcephalomannine, and 10-Deacetyltaxol: New Antitumor Taxanes From Taxus wallichiana. J. Nat. Prod. 44, 312–319Manli Zhang, Xinhua Lu, Jing Zhang, Shaoxia Zhang, Mei Dong, Changhong Huo, Qingwen Shi, Yucheng Gu, and Bin Cong (2010). Taxanes from the leaves of Taxus cuspidata. Chemistry of Natural Compounds 46, 53–58.
Species: Taxus
Notes: This compound was also identified by McLaughlin, J.L., Miller, R.W., Powell, R.G., and Smith, C.R. (1981). 19-Hydroxybaccatin III, 10-Deacetylcephalomannine, and 10-Deacetyltaxol: New Antitumor Taxanes From Taxus wallichiana. J. Nat. Prod. 44, 312–319 however, Zhang et al has more complete NMR data. The 13C data at Ph 3' m, p positions not well defined, see literature for details.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 2 | 5.73 | d | 7.4 |
| 3 | 3.91 | d | 7.5 |
| 5 | 4.9 | dd | 9, 3.9 |
| 6a | 2.32 | m | |
| 6b | 2.32 | m | |
| 7 | 3.66 | br ddd | 12.3, 4.8, 1.8 |
| 7-OH | 4.73 | d | 12.2 |
| 10 | 5.42 | s | |
| 10-OH | 4.11 | br s | |
| 13 | 6.23 | m | |
| 14a | 2.38 | m | |
| 14b | 2.22 | m | |
| 16 | 1.21 | s | |
| 17 | 1.08 | s | |
| 18 | 1.74 | s | |
| 19 | 1.72 | s | |
| 20ab | 4.39 | s | |
| OAc | 2.51 | s | |
| Bz-2 o | 8.16 | d | 7.8 |
| Bz-2 m | 7.52 | t | 7.8 |
| Bz-2 p | 7.61 | t | 7.8 |
| 2' | 4.79 | br s | |
| 2'-OH | 3.44 | br | |
| 3' | 5.79 | dd | 9.2, 2.7 |
| Ph 3' o | 7.47 | ||
| Ph 3' m, p | 7.4 | ||
| Ph 6' o | 7.72 | d | |
| Ph 6' m | 7.37 | ||
| Ph 6' p | 7.36 |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 79.1 |
| 2 | 75.4 |
| 3 | 40.3 |
| 4 | 81.9 |
| 5 | 82.6 |
| 6 | 35.4 |
| 7 | 75.8 |
| 8 | 57.1 |
| 9 | 214.9 |
| 10 | 77.7 |
| 11 | 135.5 |
| 12 | 137.7 |
| 13 | 72.5 |
| 14 | 36.3 |
| 15 | 42.4 |
| 16 | 26 |
| 17 | 20.5 |
| 18 | 14.3 |
| 19 | 16.6 |
| 20 | 77.7 |
| OAc-CH3 | 22.5 |
| OAc-C | 172.3 |
| CO-2 | 166.9 |
| Bz-2 o | 130.2 |
| Bz-2 m | 128.8 |
| Bz-2 p | 133.7 |
| 2' | 73.1 |
| 3' | 54.9 |
| Ph 3' o | 126.5 |
| Ph 3' m, p | 128.5 |
| CO 5' | 166.9 |
| Ph 6' o | 126.5 |
| Ph 6' m | 128.6 |
| Ph 6' p | 128.6 |
