N-Acetyl-N-debenzoyltaxol

N-Acetyl-N-debenzoyltaxol

Common Name: N-Acetyl-N-debenzoyltaxol

Synonyms:

CAS Registry Number: 173101-48-9

InChI: InChI=1S/C42H49NO14/c1-21-27(55-38(51)32(48)31(43-22(2)44)25-14-10-8-11-15-25)19-42(52)36(56-37(50)26-16-12-9-13-17-26)34-40(7,28(47)18-29-41(34,20-53-29)57-24(4)46)35(49)33(54-23(3)45)30(21)39(42,5)6/h8-17,27-29,31-34,36,47-48,52H,18-20H2,1-7H3,(H,43,44)/t27-,28-,29+,31-,32+,33+,34-,36-,40+,41-,42+/m0/s1

InChIKey: InChIKey=NANZRVGWMMGVIQ-IWMLREIISA-N

Formula: C42H49N1O14

Molecular Weight: 791.84

Exact Mass: 791.3153

NMR Solvent: CDCl3

MHz: 500.0

Calibration: Residual solvent 7.25 ppm and 77.0 ppm for proton and carbon respectively.

NMR references: Zhang, J., Sauriol, F., Mamer, O., and Zamir, L.O. (2000). Taxoids from the needles of the Canadian yew. Phytochemistry 54, 221–230.

Species: Taxus

Notes:

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.68 d 7.1
3 3.79 d 7.1
5 4.93 d 8.1
6a 2.54 ddd 15.4, 10.5, 6.8
6b 1.86 m
7 4.4 dd 10.5, 6.8
10 6.28 s
13 6.23 m
14 2.29 m
16 1.27 s
17 1.15 s
18 1.82 s
19 1.68 s
20a 4.3 d 8.5
20b 4.19 d 8.5
OAc 2.33 s
OAc 2.25 s
OBz o 8.11 d 8
OBz m 7.51 t 7.8
OBz p 7.62 t 8
2' 4.67 d 2.3
3' 5.55 dd 8.8, 2.3
3' Ph 7.38 m
NH 4' 6.23 m
Me 6' 2.01 s

Carbon NMR Peaks

Position PPM
1 78.9
2 74.8
3 45.5
4 81.1
5 84.4
6 35.3
7 72.1
8 58.3
9 203.7
10 75.3
11 133.1
12 141.9
13 72.3
14 35.3
15 43
16 26.6
17 21.6
18 14.5
19 9.3
20 76.4
OAc 22.5
OAc 170.1
OAc 20.5
OAc 171.2
OBz 1" 166.9
OBz o 130.1
OBz m 128.5
OBz p 133.7
C=O 1' 172.7
2' 72.9
3' 54.5
3' Ph 128.5
3' Ph 128.7
3' Ph 126.8
C=O 5' 169.9
Me 6' 23