9α,13α-dihydroxy-2α,10β-diacetoxy-5α-cinnamoyloxy-taxa-4(20),11-diene

9α,13α-dihydroxy-2α,10β-diacetoxy-5α-cinnamoyloxy-taxa-4(20),11-diene

Common Name: 9α,13α-dihydroxy-2α,10β-diacetoxy-5α-cinnamoyloxy-taxa-4(20),11-diene

Synonyms: 2α,10β-Diacetoxy-5α-cinnamoyloxytaxa-4(20),11-diene-9α,13α-diol

CAS Registry Number:

InChI: InChI=1S/C33H42O8/c1-18-24(36)17-23-29(39-20(3)34)28-19(2)25(41-26(37)14-13-22-11-9-8-10-12-22)15-16-33(28,7)31(38)30(40-21(4)35)27(18)32(23,5)6/h8-14,23-25,28-31,36,38H,2,15-17H2,1,3-7H3/b14-13+/t23-,24-,25-,28-,29+,30+,31-,33+/m0/s1

InChIKey: InChIKey=RGYXMTHCUWREBB-UARSWVRWSA-N

Formula: C33H40O8

Molecular Weight: 564.66

Exact Mass: 564.2723

NMR Solvent: CDCl3

MHz: 500.0

Calibration: Solvent 7.25 ppm for proton and 77.0 ppm for carbon.

NMR references: Shi, Q.W., Sauriol, F., Mamer, O., and Zamir, L.O. (2003). New minor taxanes analogues from the needles of Taxus canadensis. Bioorganic & Medicinal Chemistry 11, 293–303.

Species: Taxus

Notes: This compound could not be found in Chemical Abstracts Sci-finder database. 13C-NMR assignments for carbon 4 are missing.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 1.76 d 9.3
2 5.41 m
3 3.31 d 5.5
5 5.42 s
6a 1.99 br d 14.6
6b 1.77 m
7a 1.9 m
7b 1.33 m
9 4.26 d 10.1
10 5.83 d 10.1
13 4.53 br dd 9.5, 5.2
14a 2.7 dt 15.8, 9.5
14b 1.59 m
16 0.98 s
17 1.57 s
18 2.31 s
19 1.09 s
20a 5.36 s
20b 5.03 s
OAc 2.1 s
OAc 2.05 s
2' 6.82 d 15.9
3' 7.72 d 15.9
Ph'-o 7.55 m
Ph'-m,p 7.38 m

Carbon NMR Peaks

Position PPM
1 48
2 71.8
3 44
5 79.5
6 28.3
7 25.7
8 44.8
9 76.1
10 76.4
11 133.3
12 141.1
13 67.8
14 32.52
15 37.3
16 31.9
17 26.3
18 16
19 17.9
20 118
OAc 21.2
OAc 21.4
OAc 170.4
OAc 169.7
1' 166.5
2' 117.8
3' 145.6
Ph' 134.7
Ph' 128.1
Ph' 128.8
Ph' 130.2