7,​9,​10-​Trideacetylbaccatin VI

7,​9,​10-​Trideacetylbaccatin VI

Common Name: 7,​9,​10-​Trideacetylbaccatin VI

Synonyms: 10-​Deacetyl-​9-​dihydro-​13-​acetylbaccatin III

CAS Registry Number: 162489-62-5

InChI: InChI=1S/C31H40O11/c1-15-19(40-16(2)32)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,25(36)23(35)22(15)28(31,4)5)20(34)12-21-30(24,14-39-21)42-17(3)33/h7-11,19-21,23-26,34-36,38H,12-14H2,1-6H3/t19-,20-,21+,23+,24-,25-,26-,29+,30-,31+/m0/s1

InChIKey: InChIKey=YLAVPGTYTCSGNI-UFJLMRSISA-N

Formula: C31H40O11

Molecular Weight: 588.64

Exact Mass: 588.2571

NMR Solvent: CDCl3

MHz: 500.0

Calibration: Proton NMR calibrated with residual solvent 7.25 ppm.

NMR references: Zamir, L.O., Nedea, M.E., Zhou, Z.-H., Bélair, S., Caron, G., Sauriol, F., Jacqmain, E., Jean, F.I., Garneau, F.-X., and Mamer, O. (1995). Taxus canadensis taxanes: structures and stereochemistry. Canadian Journal of Chemistry 73, 655–665.

Morita, H., Wei, L., Gonda, A., Takeya, K., and Itokawa, H. (1997). A taxoid from Taxus cuspidata var. nana. Phytochemistry 46, 583–586.

Species: Taxus

Notes: There is confusion in the reference by Zamir et al., over the stereochemistry of position 7. See both references for details. Peak shape and coupling constant was not clear in literature for proton at position 13 and therefore we left these blank.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.83 d 6.3
3 3.21 d 5.8
5 4.93 d 9.8
6A 2.6 m
6B 1.8 m
7 4.35 dd 10.3, 7.7
9 4.54 d 10.3
10 4.83 d 10.3
13 6.18
14 2.2 m
16 1.31 s
17 1.66 s
18 1.81 s
19 1.58 s
20A 4.31 d 8.3
20B 4.16 d 8.3
Ac 2.29 s
Ac 2.18 s
Benzoyl 8.08 d 8.3
Benzoyl 7.47 t 7.7
Benzoyl 7.6 t

Carbon NMR Peaks

Position PPM
1 79.03
2 73.7
3 46.92
4 82.02
5 83.96
6 38.08
7 74.42
8 44.41
9 78.34
10 70.85
11 137.69
12 137.5
13 70.06
14 35.37
15 43.09
16 22.32
17 28.58
18 14.89
19 12.41
20 76.67
4-Ac 22.87
4-Ac-CO 169.45
13-Ac 21.3
13-Ac-CO 170.56
2-Bz 133.66
2-Bz 128.63
2-Bz 130.1
2-Bz 129.37
2-Bz 167.07