1β,9α-Dihydroxy-4β,20-epoxy-2α,5α,7β,10β,13α-pentaacetoxy-tax-11-ene

1β,9α-Dihydroxy-4β,20-epoxy-2α,5α,7β,10β,13α-pentaacetoxy-tax-11-ene

Common Name: 1β,9α-Dihydroxy-4β,20-epoxy-2α,5α,7β,10β,13α-pentaacetoxy-tax-11-ene

Synonyms: 2α,5α,7β,10β,13α-pentaacetoxy-4β,20-epoxytax-11-ene-1β,9α-diol

CAS Registry Number: 151625-76-2

InChI: InChI=1S/C30H42O13/c1-13-19(39-14(2)31)11-30(37)26(43-18(6)35)24-28(9,25(36)23(42-17(5)34)22(13)27(30,7)8)20(40-15(3)32)10-21(41-16(4)33)29(24)12-38-29/h19-21,23-26,36-37H,10-12H2,1-9H3/t19-,20-,21-,23+,24-,25-,26-,28+,29+,30+/m0/s1

InChIKey: InChIKey=MOYRAVFYAVRDRE-RRHJOLCQSA-N

Formula: C30H42O13

Molecular Weight: 610.65

Exact Mass: 610.2625

NMR Solvent: acetone-d6

MHz: 500.0

Calibration: Residual solvent 2.04 ppm and 29.8 ppm for proton and carbon respectively.

NMR references: Chu, A., Davin, L.B., Zajicek, J., Lewis, N.G., and Croteau, R. (1993). Intramolecular acyl migrations in taxanes from Taxus brevifolia. Phytochemistry 34, 473–476.

Species: Taxus

Notes:

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.38 d 3.4
3 3.17 d 3.4
5 4.1 t 2.8
6α 1.74 ddd 14.3, 4.4, 2.8
6β 2.1 m
7 5.47 dd 12.1, 4.4
9 4.44 d 10.7
10 6.07 d 10.7
13 6.03 m
14α 2.03 m
14β 2.48 dd 14.9, 9.6
16 1.19 s
17 1.49 s
18 2.22 d 1.5
19 1.4 s
20 2.29 d 5.2
20' 3.6 d 5.2
COMe 1.92 s
COMe 1.95 s
COMe 2.02 s
COMe 2.12 s
COMe 2.23 s

Carbon NMR Peaks

Position PPM
1 75.8
2 72.5
3 41.9
4 59.2
5 78.6
6 31.9
7 70
8 47.1
9 76.5
10 74.3
11 137.7
12 139.7
13 71.8
14 39.9
15 44.2
16 28.6
17 22.8
18 15.7
19 15.1
20 50.3
COMe, C-7 21
COMe, C-2 21.1
COMe, C-13 21.5
COMe, C-10 21.6
COMe, C-5 21.9
COMe, C-2 169.6
COMe, C-5 169.9
COMe, C-10 170.2
COMe, C-7 170.3
COMe, C-13 171