Baccatin V

Baccatin V

Common Name: Baccatin V

Synonyms: 7-​epi-​baccatin III

CAS Registry Number: 31077-81-3

InChI: InChI=1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3/t19-,20+,21+,23+,24-,26-,29+,30-,31+/m0/s1

InChIKey: InChIKey=OVMSOCFBDVBLFW-QZDKRUOYSA-N

Formula: C31H38O11

Molecular Weight: 586.63

Exact Mass: 586.2414

NMR Solvent: CDCl3

MHz: 500.0

Calibration: TMS

NMR references: Zhan, J., Zhang, Y., Ning, L., Ye, M., Guo, H., and Guo, D. Microbial transformation of taxol by Pseudomonas aeruginosa AS 1.860. Chinese Journal of Applied & Environmental Biology 9, 429–432.

Rojas, A.C., De Marcano, D., Méndez, B., and de Méndez, J. (1983). Carbon-13 NMR spectra of taxane-type diterpenes: Oxiranes and oxetanes. Org. Magn. Reson. 21, 257–260.

Species: Taxus

Notes: Relative stereochemistry not reported for protons at positions 6 and 14.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.72 d 7.5
3 4.03 d 7.5
5 4.95 dd 9, 3.5
6 2.3 m
6 2.35 m
7 3.69 m
10 6.83 s
13 4.83 m
14 2.27 m
14 2.34 m
16 1.12 s
17 1.07 s
18 2.01 s
19 1.64 s
20 4.34 d 8
20 4 d 8.5
2 - OCOC6H5 8.25 d 7
2 - OCOC6H5 7.5 t 2.5
2 - OCOC6H5 7.62 d 7.5
4 - OCOCH3 2.37 s
10 - OCOCH3 2.21 s

Carbon NMR Peaks

Position PPM
1 75.4
2 79.1
3 40.7
4 81.9
5 82.7
6 39
7 75.8
8 57.7
9 207.9
10 77.7
11 132.1
12 144.4
13 67.6
14 35.4
15 42.2
16 20.4
17 26.4
18 15.6
19 16.3
20 75.8
OAc 20.9
OAc 22.6
OAc 169.8
OAc 172.6
OBz C=O 167.2
OBz 1' 129.7
OBz 2' 128.8
OBz 3' 130.3
OBz 4' 133.9