14β-​Benzoyloxy-​13-​deacetylbaccatin IV

14β-​Benzoyloxy-​13-​deacetylbaccatin IV

Common Name: 14β-​Benzoyloxy-​13-​deacetylbaccatin IV

Synonyms: 13-Deacetyl-14β-benzoyloxybaccatin IV

CAS Registry Number: 705973-68-8

InChI: InChI=1S/C37H46O15/c1-17-26-28(48-19(3)39)31(49-20(4)40)35(9)24(47-18(2)38)15-25-36(16-46-25,52-22(6)42)29(35)32(50-21(5)41)37(45,34(26,7)8)30(27(17)43)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=SNLZFHVXSDOFFU-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: 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 5.72 d 6
3 3.22 d 6
5 4.97 d 6.2
6 2.45 m
6 1.75 m
7 5.61 dd 9.8, 7.7
9 6.02 d 11.4
10 6.21 d 11.4
13 5 d 5.8
14 5.68 d 5.8
16 1.68 s
17 1.31 s
18 2.18 s
19 1.56 s
20 4.51 d 7.9
20 4.15 d 7.9
OCOPh o 8.05 d 8
OCOPh m 7.5 t 8
OCOPh p 7.62 t 7.4
OAc 2.2 s
OAc 2.18 s
OAc 2.11 s
OAc 1.99 s
OAc 1.98 s

Carbon NMR Peaks

Position PPM
1 77.5
2 72.9
3 47.7
4 81.3
5 84.3
6 35.4
7 72.7
8 46.5
9 75.4
10 71.6
11 134.5
12 143.5
13 75.5
14 76.5
15 43.3
16 28.5
17 23.8
18 15.8
19 12.9
20 75.5
OCOPh 166
OCOPh i 131.7
OCOPh o 130.6
OCOPh m 129.2
OCOPh p 133.7
OAc 171.3
OAc 171.1
OAc 170.8
OAc 170.2
OAc 169.3
OAc 23
OAc 21.4
OAc 21.4
OAc 20.9
OAc 20.8