Baccatin III 13-cinnamate

Baccatin III 13-cinnamate

Common Name: Baccatin III 13-cinnamate

Synonyms: deaminoacylcinnamoyltaxol

CAS Registry Number: 220932-65-0

InChI: InChI=1S/C40H44O12/c1-22-27(50-30(44)18-17-25-13-9-7-10-14-25)20-40(47)35(51-36(46)26-15-11-8-12-16-26)33-38(6,28(43)19-29-39(33,21-48-29)52-24(3)42)34(45)32(49-23(2)41)31(22)37(40,4)5/h7-18,27-29,32-33,35,43,47H,19-21H2,1-6H3/b18-17+/t27-,28-,29+,32+,33-,35-,38+,39-,40+/m0/s1

InChIKey: InChIKey=PPZXDJGRIUOJEB-ODILUHENSA-N

Formula: C40H44O12

Molecular Weight: 716.77

Exact Mass: 716.2833

NMR Solvent: CDCl3

MHz: 400.0

Calibration: Not mentioned in reference.

NMR references: Yang, S.-J., Fang, J.-M., and Cheng, Y.-S. (1999). Abeo-taxanes from Taxus mairei. Phytochemistry 50, 127–130.

Species: Taxus

Notes: Relative stereochemistry not reported for protons at position 14. Protons on cinnamate and benzoate not assigned. Numerous unassigned carbons on benzoate and cinnamate.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.66 d 6.8
3 3.85 d 6.8
5 4.96 d 8.1
6 2.55 m
7 4.45 m
10 6.32 s
13 6.18 t 8.4
14 2.22 dd 15.2, 8.4
14 2.41 dd 15.2, 8.4
16 1.22 s
17 1.11 s
18 2 s
19 1.66 s
20 4.31 d 8.4
20 4.15 d 8.4
AcO 2.23 s
AcO 2.26 s
6.51 d 16
7.43 m
7.46 m
7.56 m
7.57 m
7.83 d 16
8.04 d 7.2

Carbon NMR Peaks

Position PPM
1 79.2
2 74.8
3 45.8
4 81
5 84.3
6 36.2
7 72.3
8 58.7
9 203.8
10 75.7
11 130.9
12 143.1
13 70
14 35.6
15 43
16 21.3
17 26.8
18 15.5
19 9.4
20 76.4
AcO 20.9
AcO 22.6
cinn. 116.7
128.2
128.6
129
129.1
130
BzO 130.9
133.7
133.8
cinn. 146.7
cinn. 166.2
BzO 166.9
AcO 169.8
AcO 171.3