Spektraris NMR
5β,20-Epoxy-1β-hydroxy-4α,7β,13α-triacetoxy-2α,9α, 10β-tribenzoxytax-11-ene
Common Name: 5β,20-Epoxy-1β-hydroxy-4α,7β,13α-triacetoxy-2α,9α, 10β-tribenzoxytax-11-ene
Synonyms: 4α,7β,13α-Triacetoxy-2α,9α,10β-tribenzoyloxy-5β,20-epoxytax-11-en-1β-ol
CAS Registry Number: 146257-41-2
InChI: InChI=1S/C47H50O14/c1-26-33(56-27(2)48)24-47(54)40(60-43(53)32-21-15-10-16-22-32)38-45(7,34(57-28(3)49)23-35-46(38,25-55-35)61-29(4)50)39(59-42(52)31-19-13-9-14-20-31)37(36(26)44(47,5)6)58-41(51)30-17-11-8-12-18-30/h8-22,33-35,37-40,54H,23-25H2,1-7H3
InChIKey: InChIKey=YVAYNAWZJXUNAL-UHFFFAOYSA-N
Formula: C47H50O14
Molecular Weight: 838.89
Exact Mass: 838.3201
NMR Solvent: CDCl3
MHz: 500.0
Calibration: TMS
NMR references: Chu, A., Zajicek, J., Davin, L.B., Lewis, N.G., and Croteau, R.B. (1992). Mixed acetoxy-benzoxy taxane esters from Taxus brevifolia. Phytochemistry 31, 4249–4252.
Species: Taxus
Notes: Carbon NMR assignments for positions 11 and 12 may be interchanged as well as positions 16 and 17.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 2 | 6.57 | d | 7.6 |
| 3 | 3.19 | d | 7.6 |
| 5 | 4.98 | d | 7.3 |
| 6α | 2.72 | m | |
| 6β | 1.84 | dd | 15.8, 8.1 |
| 7 | 5.7 | t | 8.1 |
| 9 | 6.58 | d | 10.8 |
| 10 | 6.78 | d | 10.8 |
| 13 | 5.74 | t | 7.9 |
| 14α | 2.47 | dd | 14.2, 7.9 |
| 14β | 2 | dd | 14.2, 7.9 |
| 16 | 1.23 | s | |
| 17 | 1.23 | s | |
| 18 | 1.98 | s | |
| 19 | 1.88 | s | |
| 20α | 4.52 | d | 7.7 |
| 20β | 4.2 | d | 7.7 |
| OAc | 1.84 | s | |
| OAc | 2.18 | s | |
| OAc | 2.21 | s | |
| m-ArH(3) | 7.2 | t | 7.6 |
| m-ArH(2) | 7.24 | t | 7.6 |
| p-ArH(3) | 7.35 | t | 7.6 |
| p-ArH(2) | 7.38 | t | 7.6 |
| m-ArH(1) | 7.5 | t | 7.6 |
| p-ArH(1) | 7.62 | t | 7.6 |
| o-ArH(3) | 7.66 | d | 7.6 |
| o-ArH(2) | 7.76 | d | 7.6 |
| o-ArH(1) | 8.05 | d | 7.6 |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 75.7 |
| 2 | 68.5 |
| 3 | 44.4 |
| 4 | 79 |
| 5 | 84.7 |
| 6 | 34.8 |
| 7 | 70.5 |
| 8 | 43.8 |
| 9 | 77.4 |
| 10 | 68.4 |
| 11 | 129.4 |
| 12 | 136.2 |
| 13 | 78.7 |
| 14 | 36.7 |
| 15 | 68.2 |
| 16 | 25.5 |
| 17 | 27.7 |
| 18 | 13.2 |
| 19 | 11.9 |
| 20 | 74.5 |
| OCOMe(1) | 21.1 |
| OCOMe(2) | 21.7 |
| OCOMe(3) | 21.9 |
| OCOMe(1) | 170 |
| OCOMe(2) | 170.6 |
| OCOMe(3) | 169 |
| OCOPh(1) | 165.9 |
| (o) OCOPh(1) | 129.6 |
| (m) OCOPh(1) | 128.6 |
| (p) OCOPh(1) | 133.5 |
| OCOPh(2) | 166.5 |
| (o) OCOPh(2) | 129.6 |
| (m) OCOPh(2) | 128 |
| (p) OCOPh(2) | 132.8 |
| OCOPh(3) | 164.4 |
| (o) OCOPh(3) | 129.2 |
| (m) OCOPh(3) | 128.3 |
| (p) OCOPh(3) | 133 |
