Spektraris NMR
Taxuspine P
Common Name: Taxuspine P
Synonyms: 2α,7β,9α,10β,13-Pentaacetoxy-11β-hydroxy-5α-(3'-N,N-dimethylamino-3'-phenyl)propionyloxytaxa-4(20),12-diene
CAS Registry Number: 175739-43-2
InChI: InChI=1S/C41H55NO13/c1-21-31(55-34(48)19-30(42(11)12)28-16-14-13-15-17-28)20-33(51-24(4)44)40(10)35(21)36(52-25(5)45)29-18-32(50-23(3)43)22(2)41(49,39(29,8)9)38(54-27(7)47)37(40)53-26(6)46/h13-17,29-31,33,35-38,49H,1,18-20H2,2-12H3/t29-,30+,31-,33-,35-,36+,37-,38-,40+,41-/m0/s1
InChIKey: InChIKey=WKBGGGLQBJFAIE-TYSRQZBFSA-N
Formula: C41H55N1O13
Molecular Weight: 769.87
Exact Mass: 769.3673
NMR Solvent: C6D6
MHz: 500.0
Calibration: Residual solvent 7.20 ppm and 123.5 ppm for proton and carbon respectively.
NMR references: Kobayashi, J., Hosoyama, H., Katsui, T., Yoshida, N., and Shigemori, H. (1996). Taxuspines N, O, and P, new taxoids from Japanese yew Taxus cuspidata. Tetrahedron 52, 5391–5396.
Species: Taxus
Notes: Carbon assignments missing for positions 4, 26, 27, 28, and NMe2.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 1 | 2.06 | m | |
| 2 | 6.14 | d | 6.6 |
| 3 | 3.99 | d | 6.6 |
| 5 | 5.24 | m | |
| 6 | 2.12 | m | |
| 7 | 5.57 | t | 8.3 |
| 9 | 5.24 | d | 4.8 |
| 10 | 5.92 | d | 4.8 |
| 14 | 2.6 | m | |
| 16 | 1.26 | s | |
| 17 | 1.62 | s | |
| 18 | 1.5 | s | |
| 19 | 1.69 | s | |
| 20a | 5.44 | s | |
| 20b | 5.46 | s | |
| 22a | 2.49 | dd | 14.5, 7.8 |
| 22b | 2.91 | dd | 14.5, 7.8 |
| 23 | 4.07 | t | 7.8 |
| 25 and 29 | 7.2 | m | |
| 26 | 7.1 | m | |
| 27 | 7.1 | m | |
| 28 | 7.1 | m | |
| NMe2 | 2.22 | s | |
| CH3CO | 2.1 | s | |
| CH3CO | 1.94 | s | |
| CH3CO | 1.78 | s | |
| CH3CO | 1.58 | s | |
| CH3CO | 1.58 | s |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 51.6 |
| 2 | 68.9 |
| 3 | 41.9 |
| 4 | 144.1 |
| 5 | 71.2 |
| 6 | 32.1 |
| 7 | 68.3 |
| 8 | 44.1 |
| 9 | 75.5 |
| 10 | 77.8 |
| 11 | 79.4 |
| 12 | 125.4 |
| 13 | 144.8 |
| 15 | 42.1 |
| 16 | 25 |
| 17 | 30.5 |
| 18 | 12 |
| 19 | 15.6 |
| 20 | 111.4 |
| 21 | 169.9 |
| 22 | 38.8 |
| 23 | 66.7 |
| 24 | 138.4 |
| 25 and 29 | 128.5 |
| CH3CO | 170.8 |
| CH3CO | 170.6 |
| CH3CO | 170.5 |
| CH3CO | 170.5 |
| CH3CO | 168.6 |
| CH3CO | 21.4 |
| CH3CO | 20.8 |
| CH3CO | 20.8 |
| CH3CO | 20.4 |
| CH3CO | 20.4 |
