Taxol D

Taxol D

Common Name: Taxol D

Synonyms: Taxcultine

CAS Registry Number: 153415-46-4

InChI: InChI=1S/C44H53NO14/c1-8-15-31(49)45-33(26-16-11-9-12-17-26)34(50)40(53)57-28-21-44(54)38(58-39(52)27-18-13-10-14-19-27)36-42(7,29(48)20-30-43(36,22-55-30)59-25(4)47)37(51)35(56-24(3)46)32(23(28)2)41(44,5)6/h9-14,16-19,28-30,33-36,38,48,50,54H,8,15,20-22H2,1-7H3,(H,45,49)/t28-,29-,30+,33-,34+,35+,36-,38-,42+,43-,44+/m0/s1

InChIKey: InChIKey=SXPIMOCRRJUHJY-MNLIZOKASA-N

Formula: C44H53N1O14

Molecular Weight: 819.89

Exact Mass: 819.3466

NMR Solvent: CDCl3

MHz: 300.0

Calibration: TMS

NMR references: Appendino, G., Cravotto, G., Enriù, R., Gariboldi, P., Barboni, L., Torregiani, E., Gabetta, B., Zini, G., and Bombardelli, E. (1994). Taxoids from the Roots of Taxus × media cv. Hicksii. J. Nat. Prod. 57, 607–613.

Species: Taxus

Notes: This compound has also been named N-Debenzoyl-N-butanoyl taxol.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.68 d 7
3 3.79 d 7
5 4.94 br d 9.2
6α 2.54 m
6β 1.86 m
7 4.4 ddd 11, 6.3, 4
10 6.29 s
13 6.24 br t 9
14α 2.3 m
14β 2.3 m
16 1.17 s
17 1.26 s
18 1.82 br s
19 1.66 s
20a 4.28 d 8.6
20b 4.2 d 8.6
Ac 2.35 s
Ac 2.26 s
2' 4.68 br s
3' 5.58 dd 9, 2.5
N-H 6.25 d 9
2" 2.18 t 7.3
3" 1.61 m
4" 0.9 t 6.7
phenyl 7.4 m
benzoate 8.1 d 7.8
benzoate 7.5 t 7.8
benzoate 7.63 t 7.8
1-OH 1.86 s
7-OH 2.43 d 4
2'-OH 3.6 d 5

Carbon NMR Peaks

Position PPM
1 78.9
2 74.96
3 45.6
4 81.13
5 84.38
6 35.62
7 72.13
8 58.56
9 203.65
10 75.58
11 138.06
12 142
13 72.39
14 35.62
15 43.21
16 21.88
17 26.8
18 14.79
19 9.56
20 76.48
Ac 171.25
Ac 170.23
Ac 22.57
Ac 20.84
1' 172.85
2' 73.1
3' 54.58
phenyl 133.18
phenyl 126.96
phenyl 128.26
phenyl 128.67
1" 172.94
2" 38.47
3" 19.11
4" 13.64
benzoate 166.9
benzoate 129.18
benzoate 130.19
benzoate 128.95
benzoate 133.67