14β-Hydroxybaccatin VI

14β-Hydroxybaccatin VI

Common Name: 14β-Hydroxybaccatin VI

Synonyms:

CAS Registry Number: 859513-89-6

InChI: InChI=1S/C37H46O15/c1-17-26-28(49-20(4)40)31(50-21(5)41)35(9)24(47-18(2)38)15-25-36(16-46-25,52-22(6)42)29(35)32(51-33(44)23-13-11-10-12-14-23)37(45,34(26,7)8)30(43)27(17)48-19(3)39/h10-14,24-25,27-32,43,45H,15-16H2,1-9H3/t24-,25+,27+,28+,29-,30-,31-,32-,35+,36-,37+/m0/s1

InChIKey: InChIKey=KEYYGWXSOSAALR-DNYCPWKRSA-N

Formula: C37H46O15

Molecular Weight: 730.75

Exact Mass: 730.2837

NMR Solvent: acetone-d6

MHz: 400.0

Calibration: Not mentioned in reference.

NMR references: Fu-Sheng, W., Li-Yan, P., Yu, Z., Kun, G., Qin-Shi, Z., and Han-Dong, S. (2003). Taxoids from the leaves and stems of Taxus chinensis. Acta Botanica Yunnanica 25, 369–376.

Species: Taxus

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

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 6.03 d 6.1
3 3.18 d 6.1
5 4.92 d 8.9
6 2.41 m
6 1.79 m
7 5.56 dd 9.8, 8
9 6.14 br s
10 6.14 br s
13 6.07 br d 6.7
14 4.28 d 6.4
OH-14 4.41 s
16 1.17 s
17 1.74 s
18 1.98 s
19 1.62 s
20 4.17 d 8
20 4.12 d 8
OCOPh o 8.11 d 8.3
OCOPh m 7.51 t 7.8
OCOPh p 7.63 t 7.4
OAc 2.37 s
OAc 2.21 s
OAc 2.13 s
OAc 2.08 s
OAc 1.98 s

Carbon NMR Peaks

Position PPM
1 76.8
2 73.3
3 47.4
4 82
5 84.2
6 35.4
7 72.5
8 46.6
9 75.4
10 71.3
11 136.6
12 138.7
13 79.2
14 70.7
15 43.6
16 28.7
17 24.5
18 14.5
19 13
20 76.4
OCOPh 166.1
OCOPh i 131
OCOPh o 130.7
OCOPh m 129.4
OCOPh p 134.1
OAc 171.3
OAc 170.9
OAc 170.8
OAc 170.3
OAc 169.4
OAc 22.8
OAc 21.4
OAc 21.1
OAc 20.8
OAc 20.8