N-​Debenzoyl-​N-​α-​methylbutyrylpaclita​xel

N-​Debenzoyl-​N-​α-​methylbutyrylpaclita​xel

Common Name: N-​Debenzoyl-​N-​α-​methylbutyrylpaclita​xel

Synonyms: N-debenzoyl-N-(2-methylbutyryl)taxol

CAS Registry Number: 159001-25-9

InChI: InChI=1S/C45H55NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32(24(29)3)42(45,6)7/h10-19,23,29-31,33-36,38,49-50,55H,9,20-22H2,1-8H3,(H,46,52)

InChIKey: InChIKey=OKEKLOJNCOIPIT-UHFFFAOYSA-N

Formula: C45H55N1O14

Molecular Weight: 833.92

Exact Mass: 833.3623

NMR Solvent: CDCl3

MHz: 400.0

Calibration: Residual solvent 7.26 ppm for proton and 77.0 ppm for carbon.

NMR references: Gabetta, B., Fuzzati, N., Orsini, P., Peterlongo, F., Appendino, G., and Vander Velde, D.G. (1999). Paclitaxel Analogues from Taxus × media cv. Hicksii. J. Nat. Prod. 62, 219–223.

Species: Taxus

Notes: Coupling constant missing from NH-3' doublet.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.69 d 7.2
3 3.79 d 7.2
5 4.95 dd 9.5, 1.8
2.55 m
1.88 m
7 4.39 m
10 6.31 s
13 6.17 tq 9.1, 9.1, 1
14 2.29 m
16 1.14 s
17 1.23 s
18 1.88 d
19 1.68 s
20α 4.29 d 8
20β 4.21 d 8
2' 4.65 br d 2.9
3' 5.59 dd 8.9, 2.9
OAc-4 2.37 s
OAc-10 2.23 s
NH-3' 7.06 d
Ph-3' 7.3 m
Bz-2 8.11
Bz-2 7.61
Bz-2 7.51
N-α-MeBu H-2 2.2 qd 6.7, 1.4
N-α-MeBu H-3a 1.64 m
N-α-MeBu H-3b 1.39 ddq 13.3, 7.5, 1.4
N-α-MeBu H-4 0.87 t 7.4
N-α-MeBu 2-Me 1.1 d 6.7

Carbon NMR Peaks

Position PPM
1 78.6
2 74.9
3 45.5
4 81
5 84.3
6 35.6
7 71.9
8 58.4
9 203.7
10 75.6
11 138.5
12 142.1
13 72
14 35.5
15 43.2
16 22.5
17 26.6
18 14
19 9.5
20 76.4
1' 172.8
2' 73.4
3' 54.4
Ph (ipso)-3' 133
Ph (ortho)-3' 126.8
Ph (meta)-3' 128.6
Ph (para)-3' 127.7
Bz-2 166.6
Bz-2 (ipso) 129.3
Bz-2 (ortho) 130.1
Bz-2 (meta) 128.7
Bz-2 (para) 133.4
OAc-4 170.1
OAc-4 22.6
OAc-10 171
OAc-10 26.8
N-MeBu C-1 176.1
N-MeBu C-2 42.9
N-MeBu C-3 27
N-MeBu C-4 14
N-MeBu 2-Me 17.4