N-Debenzoyl-N-propanoyl-10-deacetylpaclitaxel

N-Debenzoyl-N-propanoyl-10-deacetylpaclitaxel

Common Name: N-Debenzoyl-N-propanoyl-10-deacetylpaclitaxel

Synonyms:

CAS Registry Number: 173101-59-2

InChI: InChI=1S/C41H49NO13/c1-7-28(45)42-30(23-14-10-8-11-15-23)32(47)37(50)53-25-19-41(51)35(54-36(49)24-16-12-9-13-17-24)33-39(6,34(48)31(46)29(21(25)2)38(41,4)5)26(44)18-27-40(33,20-52-27)55-22(3)43/h8-17,25-27,30-33,35,44,46-47,51H,7,18-20H2,1-6H3,(H,42,45)/t25-,26-,27+,30-,31+,32+,33-,35-,39+,40-,41+/m0/s1

InChIKey: InChIKey=ZOIZSANARCWOGD-ANYOQAFTSA-N

Formula: C41H49N1O13

Molecular Weight: 763.83

Exact Mass: 763.3204

NMR Solvent: CDCl3

MHz: 200.0

Calibration: TMS

NMR references: Gabetta, B., Orsini, P., Peterlongo, F., and Appendino, G. (1998). Paclitaxel analogues from Taxus baccata. Phytochemistry 47, 1325–1329.

Species: Taxus

Notes:

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.68 d 7.2
3 3.89 d 7.2
5 4.92 dd 9.5, 2.1
6α 2.56 ddd 14.5, 11.5, 4.9
6β 1.8 m
7 4.22 m
10 5.19 s
13 6.18 dd 9, 8.9
14 2.28 m
16 1.12 s
17 1.23 s
18 1.81 br s
19 1.75 s
20 4.22 m
2' 4.76 dd 4.5, 2.5
3' 5.56 dd 9.1, 2.5
NH-COCH2R 2.23 q 7.7
NH-COCH2CH2R 1.1 t 7.6
4-OAc 2.34 s
3' NH 6.36 d 9.1
Bz 8.1 d 8
Bz 7.62 t 8
Bz 7.52 t 8
Ph 7.45 m

Carbon NMR Peaks

Position PPM
1 78.2
2 74.1
3 45.9
4 80.6
5 83.7
6 35.3
7 71.5
8 57.2
9 211
10 74.3
11 135.7
12 137.8
13 72.7
14 36.5
15 42.6
16 20.2
17 26
18 13.8
19 9.3
20 76.2
1' 172.3
2' 71.9
3' 54
3'-Ph 137.6
3'-Ph 126.5
3'-Ph 128.5
3'-Ph 127.8
4-OAc 169.9
4-OAc 22
NH-COR 173.2
NH-COCH2R 29.1
NH-COCH2CH2R 9.3
Bz 166.5
Bz 128.8
Bz 129.7
Bz 128.3
Bz 133.3