13-Acetyl-9-dihydrobaccatin III

13-Acetyl-9-dihydrobaccatin III

Common Name: 13-Acetyl-9-dihydrobaccatin III

Synonyms: 7,9-dideacetylbaccatin VI

CAS Registry Number: 142203-65-4

InChI: InChI=1S/C33H42O12/c1-16-21(42-17(2)34)14-33(40)28(44-29(39)20-11-9-8-10-12-20)26-31(7,22(37)13-23-32(26,15-41-23)45-19(4)36)27(38)25(43-18(3)35)24(16)30(33,5)6/h8-12,21-23,25-28,37-38,40H,13-15H2,1-7H3/t21-,22-,23+,25+,26-,27-,28-,31+,32-,33+/m0/s1

InChIKey: InChIKey=WPPPFZJNKLMYBW-FAEUQDRCSA-N

Formula: C33H42O12

Molecular Weight: 630.68

Exact Mass: 630.2676

NMR Solvent: CDCl3

MHz: 500.0

Calibration: solvent

NMR references: Gunawardana, G.P., Premachandran, U., Burres, N.S., Whittern, D.N., Henry, R., Spanton, S., and McAlpine, J.B. (1992). Isolation of 9-Dihydro-13-acetylbaccatin III from Taxus canadensis. J. Nat. Prod. 55, 1686–1689.

Species: Taxus

Notes: In Gunanwardana et al., this compound is named 9-dihydro-13-acetylbaccatin III and assignments are given in both CDCl3 and CD3OD, however we only include CDCl3 assignments in our database. This compound was also reported in (Zamir, L.O., Nedea, M.E., Bélair, S., Sauricol, F., Mamer, O., Jacqmain, E., Jean, F.I., and Garneau, F.X. (1992). Taxanes isolated from Taxus canadensis. Tetrahedron Letters 33, 5173–5176.) and named 7,9-diacetyl baccatin VI.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.76 d 5.95
3 3.05 d 5.95
5 4.96 dd 8.72, 1.3
6α 2.53 ddd 14.8, 9.1, 7.5
6β 1.96 ddd 14.8, 9.8, 1.3
7 4.45 m
9 4.45 d 10.9
10 6.2 d 10.9
13 6.17 m
14α 2.2 m
14β 2.2 m
16 1.25 s
17 1.67 s
18 1.92 d 1.4
19 1.89 s
20α 4.32 d 8.3
20β 4.17 d 8.3
o-Ph 8.09 dd 6.7, 1.4
m-Ph 7.46 m
p-Ph 7.62 m
4-COCH3 2.3 s
10-COCH3 2.1
13-COCH3 2.2

Carbon NMR Peaks

Position PPM
1 79.51
2 74.3
3 49.83
4 82.85
5 84.83
6 38.66
7 74.65
8 45.5
9 77.51
10 73.96
11 135.74
12 140.26
13 70.68
14 36.1
15 43.8
16 23.34
17 29.04
18 15.59
19 13.25
20 77.32
2-CO 167.75
q-Ph 130
o-Ph 130.79
m-Ph 129.37
p-Ph 134.42
4-COCH3 170.13
4-COCH3 23.57
10-COCH3 171.37
10-COCH3 21.96
13-COCH3 171.23
13-COCH3 22.07