2α,​17-​Dihydroxy-​9α,​10β,​13α-​triacetoxy-​5α-​(3'-​N,​N-​dimethylamino-​3'-​phenyl)​propionyloxytaxa-​4(20)​,​11-​diene

2α,​17-​Dihydroxy-​9α,​10β,​13α-​triacetoxy-​5α-​(3'-​N,​N-​dimethylamino-​3'-​phenyl)​propionyloxytaxa-​4(20)​,​11-​diene

Common Name: 2α,​17-​Dihydroxy-​9α,​10β,​13α-​triacetoxy-​5α-​(3'-​N,​N-​dimethylamino-​3'-​phenyl)​propionyloxytaxa-​4(20)​,​11-​diene

Synonyms: 9α,10β,13α-Triacetoxy-5α-[(R)-3'-dimethylamino-3'-phenylpropanoyloxy]taxa-4(20),11diene-2α,17-diol

CAS Registry Number: 824951-58-8

InChI: InChI=1S/C37H51NO10/c1-20-28(48-30(43)18-27(38(8)9)25-13-11-10-12-14-25)15-16-36(6)31(20)33(44)26-17-29(45-22(3)40)21(2)32(37(26,7)19-39)34(46-23(4)41)35(36)47-24(5)42/h10-14,26-29,31,33-35,39,44H,1,15-19H2,2-9H3/t26?,27-,28+,29+,31+,33-,34-,35+,36-,37?/m1/s1

InChIKey: InChIKey=DHWBNTVVWYKRRR-GRKXZQKMSA-N

Formula: C37H51N1O10

Molecular Weight: 669.8

Exact Mass: 669.3513

NMR Solvent: acetone-d6

MHz: 500.0

Calibration: Residual solvent 2.04ppm and 77.0ppm for proton and carbon spectra respectively.

NMR references: Shi, Q., Ji, X., Lesimple, A., Sauriol, F., and Zamir, L.O. (2004). Taxanes with C-5-amino-side chains from the needles of Taxus canadensis. Phytochemistry 65, 3097–3106.

Species: Taxus

Notes: Aromatic protons not well described. Side chain protons and carbons not reported, see reference for details. Carbon nmr data missing for position 4.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 2.55 m
2 4.21 br d 5.5
3 2.92 d 5.5
5 5.12 br t 2.4
6 1.27 m
7 1.46 m
9 5.63 d 10.8
10 5.95 d 10.8
13 5.89 m
14a 2.46 ddd 14.7, 9.8, 9.6
14b 1.47 dd 14.7, 7.5
16 1.23 s
17a 4.48 br d 11.9
17b 3.98 br d 11.9
18 2.22 br s
19 0.82 s
20a 5.89 br s
20b 5.21 br s
OAc 2.02 s
OAc 1.96 s
Ph 7.5 m

Carbon NMR Peaks

Position PPM
1 45.6
2 70.4
3 45.4
5 79.7
6 32.5
7 28.2
8 45
9 77.7
10 72.5
11 134.1
12 139.2
13 70.8
14 28.3
15 44.6
16 25.6
17 65.9
18 16.2
19 18.2
20 120.9
OAc 21.7
OAc 171
OAc 21.7
OAc 170.2