Spektraris NMR
2α,10β-Dibenzoxy-5β,20-epoxy-1β-hydroxy-4α,7β,9α,13α-tetraacetoxy-tax-11-ene
Common Name: 2α,10β-Dibenzoxy-5β,20-epoxy-1β-hydroxy-4α,7β,9α,13α-tetraacetoxy-tax-11-ene
Synonyms: 4α,7β,9α,13α-Tetraacetoxy-2α,10β-dibenzoyloxy-5β,20-epoxytax-11-en-1β-ol
CAS Registry Number: 146257-42-3
InChI: InChI=1S/C42H48O14/c1-22-29(51-23(2)43)20-42(49)36(55-38(48)28-17-13-10-14-18-28)34-40(8,30(52-24(3)44)19-31-41(34,21-50-31)56-26(5)46)35(53-25(4)45)33(32(22)39(42,6)7)54-37(47)27-15-11-9-12-16-27/h9-18,29-31,33-36,49H,19-21H2,1-8H3
InChIKey: InChIKey=OKQYLPFYPKMSMJ-UHFFFAOYSA-N
Formula: C42H48O14
Molecular Weight: 776.82
Exact Mass: 776.3044
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: Two protons were assigned to position 20β, therefore we reported each proton as being at position 20 without distinction. 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 | 6.46 | d | 7.9 |
| 3 | 3.13 | d | 7.9 |
| 5 | 4.98 | d | 8.2 |
| 6α | 2.56 | m | |
| 6β | 1.91 | dd | 15.6, 8.5 |
| 7 | 5.63 | t | 8.5 |
| 9 | 6.3 | d | 10.7 |
| 10 | 6.62 | d | 10.7 |
| 13 | 5.7 | t | 7.6 |
| 14α | 2.43 | dd | 14.3, 7.6 |
| 14β | 1.96 | dd | 14.3, 7.6 |
| 16 | 1.18 | s | |
| 17 | 1.18 | s | |
| 18 | 1.96 | s | |
| 19 | 1.77 | s | |
| 20 | 4.48 | d | 7.9 |
| 20 | 4.16 | d | 7.9 |
| OAc (1) | 1.77 | s | |
| OAc (2) | 2.16 | s | |
| OAc (3) | 2.1 | s | |
| OAc (4) | 2.19 | s | |
| m-ArH(2) | 7.74 | t | 7.6 |
| p-ArH(2) | 7.57 | t | 7.6 |
| m-ArH(1) | 7.49 | t | 7.6 |
| p-ArH(1) | 7.62 | t | 7.6 |
| o-ArH(2) | 7.87 | d | 7.6 |
| o-ArH(1) | 8.02 | d | 7.6 |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 75.6 |
| 2 | 68.2 |
| 3 | 44.9 |
| 4 | 79.4 |
| 5 | 84.5 |
| 6 | 34.8 |
| 7 | 70.5 |
| 8 | 43.6 |
| 9 | 76.4 |
| 10 | 68.5 |
| 11 | 129.9 |
| 12 | 136 |
| 13 | 78.7 |
| 14 | 36.7 |
| 15 | 68.3 |
| 16 | 25.4 |
| 17 | 27.7 |
| 18 | 12.4 |
| 19 | 11.9 |
| 20 | 74.5 |
| OCOMe(1) | 20.6 |
| OCOMe(2) | 21.4 |
| OCOMe(3) | 21.1 |
| OCOMe(4) | 21.9 |
| OCOMe(1) | 169.8 |
| OCOMe(2) | 169.8 |
| OCOMe(3) | 169 |
| OCOMe(4) | 170.7 |
| OCOPh(1) | 165.8 |
| (o) OCOPh(1) | 129.7 |
| (m) OCOPh(1) | 128.6 |
| (p) OCOPh(1) | 133.5 |
| OCOPh(2) | 164 |
| (o) OCOPh(2) | 129.5 |
| (m) OCOPh(2) | 128.8 |
| (p) OCOPh(2) | 133.4 |
