14β-​Benzoyloxy-​2-​deacetylbaccatin VI

14β-​Benzoyloxy-​2-​deacetylbaccatin VI

Common Name: 14β-​Benzoyloxy-​2-​deacetylbaccatin VI

Synonyms: 2-Deacetyl-14β-benzoyloxybaccatin IV

CAS Registry Number: 705973-69-9

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)30(43)37(45,34(26,7)8)32(27(17)48-19(3)39)51-33(44)23-13-11-10-12-14-23/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=ZZJVBWJAVYPFDJ-PRWXGGKJSA-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: Wang, F.-S., Peng, L.-Y., Zhao, Y., Xu, G., Zhao, Q.-S., and Sun, H.-D. (2004). Three New Oxetane-Ring-Containing Taxoids from Taxus chinensis. J. Nat. Prod. 67, 905–907.

Species: Taxus

Notes: Relative stereochemistry not reported for protons at position 6.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 4.17 dd 9.3, 6
3 2.95 d 6
5 4.97 d 8.2
6 2.44 m
6 1.81 m
7 5.53 dd 9.8, 7.8
9 5.9 d 11.4
10 6.14 d 11.4
13 6.46 dd 6.7, 1.6
14 5.17 d 6.7
16 1.23 s
17 1.66 s
18 2.01 s
19 1.62 s
20 4.62 d 8.8
20 4.55 d 8.8
OCOPh o 8.04 d 8.3
OCOPh m 7.53 t 8
OCOPh p 7.66 t 7.5
OAc 2.23 s
OAc 2.13 s
OAc 2.11 s
OAc 2.08 s
OAc 2.06 s

Carbon NMR Peaks

Position PPM
1 78.5
2 75.3
3 47.9
4 83
5 83.7
6 35.5
7 72.8
8 46.6
9 75.4
10 71.3
11 136.8
12 138
13 74.2
14 73.6
15 43.7
16 28.6
17 23.9
18 15.1
19 12.9
20 77.9
OCOPh 167.8
OCOPh i 134.3
OCOPh o 130.6
OCOPh m 129.4
OCOPh p 134.4
OAc 171
OAc 170.9
OAc 170.6
OAc 170.3
OAc 169.4
OAc 22.8
OAc 21.4
OAc 20.9
OAc 20.8
OAc 20.8