14β-​Benzoyloxybaccatin IV

14β-​Benzoyloxybaccatin IV

Common Name: 14β-​Benzoyloxybaccatin IV

Synonyms:

CAS Registry Number: 705973-67-7

InChI: InChI=1S/C39H48O16/c1-18-28-30(51-21(4)42)32(52-22(5)43)37(10)26(49-19(2)40)16-27-38(17-48-27,55-24(7)45)31(37)34(53-23(6)44)39(47,36(28,8)9)33(29(18)50-20(3)41)54-35(46)25-14-12-11-13-15-25/h11-15,26-27,29-34,47H,16-17H2,1-10H3/t26-,27+,29+,30+,31-,32-,33-,34-,37+,38-,39+/m0/s1

InChIKey: InChIKey=VYMBRMWJTFHPGO-LNZPRBBBSA-N

Formula: C39H48O16

Molecular Weight: 772.79

Exact Mass: 772.2942

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 5.77 d 6
3 3.18 d 6
5 4.99 d 9
6 2.15 m
6 1.75 m
7 5.57 dd 9.7, 7.8
9 6.05 d 11.3
10 6.18 d 11.3
13 6.36 d 6.3
14 5.71 d 6.3
16 1.43 s
17 1.75 s
18 2.01 s
19 1.58 s
20 4.53 d 7.9
20 4.18 d 7.9
OCOPh o 8.05 d 8
OCOPh m 7.5 t 7.8
OCOPh p 7.62 t 7.4
OAc 2.15 s
OAc 2.12 s
OAc 2.11 s
OAc 2.02 s
OAc 1.99 s
OAc 1.97 s

Carbon NMR Peaks

Position PPM
1 78.3
2 71.7
3 47.6
4 81.7
5 84.3
6 35.4
7 72.5
8 46.7
9 73.4
10 71.3
11 136.5
12 138.6
13 75.4
14 72.7
15 45.3
16 28.4
17 24
18 15.2
19 12.9
20 76.6
OCOPh 165.7
OCOPh i 131.1
OCOPh o 130.6
OCOPh m 129.3
OCOPh p 133.7
OAc 171.4
OAc 171.1
OAc 171
OAc 170.9
OAc 170.7
OAc 170.3
OAc 23
OAc 21.4
OAc 21.4
OAc 21.4
OAc 21
OAc 20.8