1-​Deoxypaclitaxel

1-​Deoxypaclitaxel

Common Name: 1-​Deoxypaclitaxel

Synonyms: 1-​Deoxytaxol

CAS Registry Number: 198990-70-4

InChI: InChI=1S/C47H51NO13/c1-25-32(59-44(56)37(52)36(28-16-10-7-11-17-28)48-42(54)29-18-12-8-13-19-29)22-31-38(60-43(55)30-20-14-9-15-21-30)40-46(6,33(51)23-34-47(40,24-57-34)61-27(3)50)41(53)39(58-26(2)49)35(25)45(31,4)5/h7-21,31-34,36-40,51-52H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33-,34+,36-,37+,38+,39+,40-,46+,47-/m0/s1

InChIKey: InChIKey=NMFSXFNXTSCWAD-IKOAQKMTSA-N

Formula: C47H51N1O13

Molecular Weight: 837.91

Exact Mass: 837.336

NMR Solvent: CDCl3

MHz: 500.0

Calibration: Not mentioned in reference.

NMR references: Shi, Q.-W., Zhao, Y.-M., Si, X.-T., Li, Z.-P., Yamada, T., and Kiyota, H. (2006). 1-Deoxypaclitaxel and abeo-Taxoids from the Seeds of Taxus mairei. J. Nat. Prod. 69, 280–283.

Species: Taxus

Notes: Coupling constants missing on a few aromatic triplets (t) due to overlap. See reference for details. 1' carbon assignment missing.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 2.14 m
2 5.65 dd 6.9, 2.9
3 3.63 d 6.9
5 4.99 d 10.2
2.56 m
1.88 m
7 4.41 m
OH-7 2.41 br
10 6.24 s
13 6.05 t 8.6
14α 1.71 m
14β 2.51 m
16 1.17 s
17 1.22 s
18 1.8 s
19 1.66 s
20a 4.38 d 8.3
20b 4.15 d 8.3
OAc-4 2.38 s
OAc-10 2.22 s
OBz-2 o 8.09 d 7.4
OBz-2 m 7.49 t
OBz-2 p 7.6 t 7.4
2' 4.78 dd 4.5, 2.4
OH-2' 3.48 br d 4.5
3' 5.77 dd 9, 2.4
Ph-3' 7.42 m
NH 6.96 d 9
NBz-3' o 7.7 d 7.6
NBz-3' m 7.41 t
NBz-3' p 7.47 t

Carbon NMR Peaks

Position PPM
1 45.4
2 72.1
3 43.3
4 81.1
5 84.2
6 35.6
7 72
8 58.9
9 204
10 75.6
11 132.9
12 140.2
13 72.1
14 26.6
15 38.3
16 30.2
17 26
18 14.8
19 9.5
20 76.6
OAc-4 22.5
OAc-4 170.1
OAc-10 20.8
OAc-10 171.2
OBz-2 ipso 165
OBz-2 o 129.8
OBz-2 m 128.5
OBz-2 p 133.5
2' 73
3' 54.7
Ph-3' 128.5
Ph-3' 126.9
NBz-3' C=O 166.9
NBz-3' o 126.9
NBz-3' m 128.8
NBz-3' p 131.7