N-Debenzoyl-N-butanoyl-10-deacetylpaclitaxel

N-Debenzoyl-N-butanoyl-10-deacetylpaclitaxel

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

Synonyms:

CAS Registry Number: 173101-47-8

InChI: InChI=1S/C42H51NO13/c1-7-14-29(46)43-31(24-15-10-8-11-16-24)33(48)38(51)54-26-20-42(52)36(55-37(50)25-17-12-9-13-18-25)34-40(6,35(49)32(47)30(22(26)2)39(42,4)5)27(45)19-28-41(34,21-53-28)56-23(3)44/h8-13,15-18,26-28,31-34,36,45,47-48,52H,7,14,19-21H2,1-6H3,(H,43,46)/t26-,27-,28+,31-,32+,33+,34-,36-,40+,41-,42+/m0/s1

InChIKey: InChIKey=WIEAOVPVSUSLBQ-QHPQOPOXSA-N

Formula: C42H51N1O13

Molecular Weight: 777.85

Exact Mass: 777.336

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 5.67 d 7
3 3.86 d 7
5 4.91 dd 9.6, 1.9
6α 2.53 ddd 14.8, 8.9, 5.5
6β 1.83 m
7 4.22 m
10 5.21 s
13 6.16 dd 9, 8.9
14 2.26 m
16 1.11 s
17 1.22 s
18 1.8 br s
19 1.73 s
20a 4.29 d 8.6
20b 4.19 d 8.6
2' 4.67 dd 4.5, 2.7
3' 5.56 dd 9, 2.7
NH-COCH2R 2.16 t 7.7
NH-COCH2CH2R 1.59 m
NH-COCH2CH2CH3 1.2 t 7.5
4-OAc 2.32 s
3' NH 6.44 d 9
Bz 8.14 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 46
4 80.6
5 83.7
6 35.3
7 71.5
8 57.2
9 210.9
10 74.4
11 135.6
12 137.8
13 72.7
14 36.4
15 42.6
16 20.2
17 26
18 13.8
19 9.3
20 76.1
1' 172.5
2' 71.9
3' 54
3'-Ph 137.7
3'-Ph 126.5
3'-Ph 128.5
3'-Ph 127.7
4-OAc 169.9
4-OAc 22
NH-COR 172.5
NH-COCH2R 38
NH-COCH2CH2R 18.6
NH-COCH2CH2CH3 13.2
Bz 166.5
Bz 128.8
Bz 129.7
Bz 128.3
Bz 133.3