9α-Hydroxy-2α,10β,13α-triacetoxy-5α-(3'-methylamino-3'-phenyl)-propionyloxytaxa-4(20),11-diene

9α-Hydroxy-2α,10β,13α-triacetoxy-5α-(3'-methylamino-3'-phenyl)-propionyloxytaxa-4(20),11-diene

Common Name: 9α-Hydroxy-2α,10β,13α-triacetoxy-5α-(3'-methylamino-3'-phenyl)-propionyloxytaxa-4(20),11-diene

Synonyms: 2α,10β,13α-Triacetoxy-5α-[(R)-3'-methylamino-3'-phenylpropanoyloxy]taxa-4(20),11-dien-9α-ol

CAS Registry Number: 525601-68-7

InChI: InChI=1S/C36H49NO9/c1-19-27(46-29(41)18-26(37-9)24-13-11-10-12-14-24)15-16-36(8)31(19)32(44-22(4)39)25-17-28(43-21(3)38)20(2)30(35(25,6)7)33(34(36)42)45-23(5)40/h10-14,25-28,31-34,37,42H,1,15-18H2,2-9H3/t25-,26+,27-,28-,31-,32+,33+,34-,36+/m0/s1

InChIKey: InChIKey=XWHQVFNFMPEWQA-ZVKWETHWSA-N

Formula: C36H49N1O9

Molecular Weight: 639.78

Exact Mass: 639.3407

NMR Solvent: CDCl3

MHz: 500.0

Calibration: Not mentioned.

NMR references: Shi, Q.-W., Sauriol, F., Mamer, O., and Zamir, L.O. (2003). New Taxanes from the Needles of Taxus canadensis. J. Nat. Prod. 66, 470–476.

Species: Taxus

Notes:

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 1.83 m
2 5.35 dd 6.6, 2.1
3 3.12 d 6.6
5 5.26 t 2.4
6a 1.62 m
6b 1.62 m
7a 1.82 m
7b 1.33 m
9 4.27 d 10
10 5.76 d 10
13 5.79 t 8.3
14a 2.48 dt 15, 9.7
14b 1.43 dd 15, 7.8
16 1.08 s
17 1.59 s
18 2.02 s
19 1.04 s
20a 5.28 s
20b 4.8 s
OAc 2.13 s
OAc 2 s
OAc 1.7 s
2' 2.8 d 6.7
3' 3.97 d 6.7
N-Me 2.3 s
Ph-o 7.34 m
Ph-m 7.34 m
Ph-p 7.27 m

Carbon NMR Peaks

Position PPM
1 48.5
2 72
3 44
4 142.4
5 79.2
6 28.3
7 25.6
8 44.8
9 75.8
10 75.7
11 133.7
12 137
13 69.9
14 28
15 37.8
16 31.2
17 27.2
18 15.1
19 18.1
20 117.7
OAc 21.3
OAc 170.6
OAc 21.5
OAc 170
OAc 20
OAc 170.9
1' 171.6
2' 42.9
3' 62.1
N-Me 34.1
Ph' 141.6
Ph-o 126.8
Ph-m 128.7
Ph-p 127.8