10-Deacetyl-10-dehydro-7-acetyltaxol A

10-Deacetyl-10-dehydro-7-acetyltaxol A

Common Name: 10-Deacetyl-10-dehydro-7-acetyltaxol A

Synonyms:

CAS Registry Number: 171864-27-0

InChI: InChI=1S/C47H49NO14/c1-25-31(60-43(56)37(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,39(53)36(51)34(25)44(47,4)5)32(59-26(2)49)22-33-46(38,24-58-33)62-27(3)50/h7-21,31-33,35,37-38,40,52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,37+,38-,40-,45+,46-,47+/m0/s1

InChIKey: InChIKey=GSTUMNHLDBUONL-LECDKBAQSA-N

Formula: C47H49N1O14

Molecular Weight: 851.89

Exact Mass: 851.3153

NMR Solvent: CDCl3

MHz: 300.0

Calibration: TMS

NMR references: Gabetta, B., Peterlongo, F., Zini, G., Barboni, L., Rafaiani, G., Ranzuglia, P., Torregiani, E., Appendino, G., and Cravotto, G. (1995). Taxanes from Taxus x media. Phytochemistry 40, 1825–1828.

Species: Taxus

Notes:

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.79 d 6.4
3 3.75 d 6.4
5 4.91 d 9
6α 2.61 ddd 14.4, 7.2, 9
6β 1.82 m
7α 5
9 5.19 dd 10.5, 7.2
13β 6.15 t 8.9
14α 2.43 dd 15, 8.9
14β 2.37 dd 15, 8.9
16 1.18 s
17 1.22 s
18 1.84 s
19 1.83 s
20a 4.33 d 8.4
20b 4.19 d 8.4
4-Ac 2.37 s
7-Ac 2.01 s
2' 4.8 dd 5.1, 2.4
2' 5.77 dd 8.8, 2.6
Ph 7.42 m
para-Ph 7.35 m
ortho-NHBz 7.71 br d 7.6
meta-NHBz 7.39 m
para-NHBz 7.48 m
para-OBz 8.01 d 7.6
meta-OBz 7.51 m
para-OBz 7.65 m
NH 7.03 d 8.9
1-OH 2.8 s
2'-OH 3.72 d 5.1

Carbon NMR Peaks

Position PPM
1 80.6
2 74.1
3 46.2
4 78.8
5 83.9
6 32.9
7 69.7
8 56.7
9 204.3
10 192.9
11 141.8
12 144.7
13 71.9
14 35.5
15 40.8
16 23.2
17 26.7
18 13.9
19 9.6
20 76.1
4-COAc 170.2
4-Ac 22.5
7-COAc 169.4
7-Ac 20.8
1' 172.5
2' 72.9
3' 55
ipso-Ph 137.8
ortho-Ph 127
meta-Ph 129
para-Ph 128.4
CONHBz 167.3
ipso-NHBz 133.5
ortho-NHBz 127
meta-NHBz 128.8
para-NHBz 132
(2)COBz 166.7
ipso-OBz 128.8
ortho-OBz 130.2
meta-OBz 128.7
para-OBz 133.9