7-Xylosyl-10-deacetyltaxol C

7-Xylosyl-10-deacetyltaxol C

Common Name: 7-Xylosyl-10-deacetyltaxol C

Synonyms: 7-(β-Xylosyl)-10-deacetyltaxol C

CAS Registry Number: 90332-65-3

InChI: InChI=1S/C49H63NO17/c1-7-8-11-20-33(53)50-35(27-16-12-9-13-17-27)38(56)44(60)64-30-22-49(61)42(66-43(59)28-18-14-10-15-19-28)40-47(6,41(58)37(55)34(25(30)2)46(49,4)5)31(21-32-48(40,24-63-32)67-26(3)51)65-45-39(57)36(54)29(52)23-62-45/h9-10,12-19,29-32,35-40,42,45,52,54-57,61H,7-8,11,20-24H2,1-6H3,(H,50,53)/t29-,30+,31+,32-,35+,36+,37-,38-,39-,40+,42+,45+,47-,48+,49-/m1/s1

InChIKey: InChIKey=XGWGQEYABFGJID-UVDBIDMBSA-N

Formula: C49H63N1O17

Molecular Weight: 938.02

Exact Mass: 937.4096

NMR Solvent: CDCl3

MHz: 500.0

Calibration: not mentioned in Shi et al., 2003.

NMR references: Shi, Q.-W., Petzke, T.L., Sauriol, F., Mamer, O., and Zamir, L.O. (2003). Taxanes in rooted cuttings vs. mature Japanese yew. Canadian Journal of Chemistry 81, 64–74.

Species: Taxus

Notes: This compound was also identified by Sénilh, V., Blechert, S., Colin, M., Guénard, D., Picot, F., Potier, P., and Varenne, P. (1984). Mise en Évidence de Nouveaux Analogues du Taxol Extraits de Taxus baccata. J. Nat. Prod. 47, 131–137.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.65 d 7.2
3 3.89 d 7.2
5 4.89 d 9.9
6a 2.73 m
6b 2.02 m
7 4.06 m
10 5.16 s
13 6.18 br t 9
14 2.27 d 9.3
16 1.23 s
17 1.1 s
18 1.83 s
19 1.81 s
20a 4.29 d 9
20 4.19 d 9
OAc 2.35
2' 4.66 br s
3' 5.57 dd 9.5, 1.8
Ph 3' o/m 7.39 m
Ph 3' p 7.34
4' NH 6.24 d 9.2
6' 2.2 t 7.7
7' 1.55 m
8' 1.25 m
9' 1.25 m
10' Me 0.83 br t
Sugar 1'' 4.06 m
2'' 3.24 m
3'' 3.48 t 8
4'' 3.68 m
5a'' 3.96 dd 11.7, 4.8
5b'' 3.25 dd 11.7, 9.8
Bz-2 o 8.09 d 8.1
Bz-2 m 7.5 t 7.7
Bz-2 p 7.61 t 7.2

Carbon NMR Peaks

Position PPM
1 78.6
2 74.5
3 46.2
5 83.8
7 81.5
8 57
9 211.7
10 74.7
11 135.7
12 138.1
13 72.3
14 35.8
15 42.9
16 26.4
17 20.7
18 14.3
19 10.8
20 76.4
OAc 22.5
OAc 170.5
2' 73.1
3' 54.4
Ph 3' 128.8
Ph 3' o/m 126.7
Ph 3' p 128.1
6' 36.6
7' 25.3
8' 31.3
9' 22.2
10' Me 13.7
Sugar 1'' 105.2
2'' 72.9
3'' 75.2
5a'' 64.9
Bz-2 o 130
Bz-2 m 128.6
Bz-2 p 133.5