2α,9α,7β,13-tetraacetoxytaxa-4(20),12-diene-5α,10β,11β-triol

2α,9α,7β,13-tetraacetoxytaxa-4(20),12-diene-5α,10β,11β-triol

Common Name: 2α,9α,7β,13-tetraacetoxytaxa-4(20),12-diene-5α,10β,11β-triol

Synonyms:

CAS Registry Number: 868663-23-4

InChI: InChI=1S/C28H40O11/c1-12-19(33)11-21(37-15(4)30)27(9)22(12)23(38-16(5)31)18-10-20(36-14(3)29)13(2)28(35,26(18,7)8)24(34)25(27)39-17(6)32/h18-19,21-25,33-35H,1,10-11H2,2-9H3/t18-,19-,21-,22-,23+,24-,25-,27+,28-/m0/s1

InChIKey: InChIKey=LOEQAIIXDSNYRZ-KSWUFBNFSA-N

Formula: C28H40O11

Molecular Weight: 552.61

Exact Mass: 552.2571

NMR Solvent: CDCl3

MHz: 500.0

Calibration: Residual solvent 7.25 ppm and 77.0 ppm for proton and carbon respectively.

NMR references: Shi, Q.W., Sauriol, F., Park, Y., Smith, V.H., Lord, G., and Zamir, L.O. (2005). First example of conformational exchange in a natural taxane enolate. Magnetic Resonance in Chemistry 43, 798–804.

Species: Taxus

Notes: This compound has two structural conformers. We tabulated the major conformer. See reference for details. As a result of conformers some reported coupling constants are approximations. We left these coupling constants out of our table.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 1.89 br d
2 5.68 d
3 3.54 d 6.9
5 4.22 m
6a 2.07 m
6b 1.76 m
7 4.74 dd 10.2, 8
9 5.05 d 4.7
10 4.31 t
OH-10 2.65 d 4.3
OH-11 2.48 s
14a 2.54 ddq 19.1, 7.7, 2.1
14b 2.36 br d 19.1
16 1.98 s
17 1.48 s
18 1.49 s
19 1.5 s
20a 5.25 s
20b 5.02 s
OAc 2.19 s
OAc 1.96 s
OAc 1.96 s
OAc 1.95 s

Carbon NMR Peaks

Position PPM
1 50.35
2 69.14
3 40.95
4 147.78
5 66.08
6 36.31
7 70.7
8 42.96
9 76.22
10 78.37
11 78.3
12 124.12
13 144.22
14 25.69
15 40.92
16 31.62
17 24.3
18 11.22
19 14.61
20 109.37
OAc 20.69
OAc 20.88
OAc 21.15
OAc 21.3
OAc 168.58
OAc 170.04
OAc 170.36
OAc 170.39