7-epi-Taxol

7-epi-Taxol

Common Name: 7-epi-Taxol

Synonyms: 7-epi-Paclitaxel

CAS Registry Number: 105454-04-4

InChI: InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32+,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1

InChIKey: InChIKey=RCINICONZNJXQF-LYTKHFMESA-N

Formula: C47H51N1O14

Molecular Weight: 853.91

Exact Mass: 853.331

NMR Solvent: CDCl3

MHz: 500.0

Calibration: TMS proton nmr. CDCl3 in 13C NMR set to 77.00 ppm relative to TMS

NMR references: Chmurny, G.N., Hilton, B.D., Brobst, S., Look, S.A., Witherup, K.M., and Beutler, J.A. (1992). 1H- and 13C-nmr Assignments for Taxol, 7-epi-Taxol, and Cephalomannine. J. Nat. Prod. 55, 414–423.

Species: Taxus

Notes: In order to distinguish aromatic protons (abbreviated Ph in table standing for phenyl) on different rings authors named the benzoyl substitutient at position 2 ring 1, the aromatic ring connected to 3' on the phenylisoserine side chain named ring 2, and the benzoyl ring connected to N ring 3. Not all aromatic protons assigned. Unassigned found in multiplet between 7.34-7.56, in our table under aromatic we report middle ppm value 7.45. Also note that protons at position H-7, H-7-OH J values differ depending on exhange of hydroxls. See literature for details.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.76 d 7.5
3 3.92 d 7.5
4-OAc 2.5 s
5 4.91 dd 9, 3.5
6 2.33 ddd 16.1, 9.2, 2.1
6 2.27 ddd 16, 5, 2.1
7 3.7 br d
7-OH 4.68 br s
10 6.8 s
10-OAc 2.19 s
13 6.23 qt 9, 1.5
14 2.42 dd 15.5, 9.3
14 2.25 dd 15.4, 9.1
16 1.15 s
17 1.19 s
18 1.79 d 1.5
19 1.67 s
20 4.39
2' 4.81 d 2.6
2'-OH 2.25
3' 5.81 dd 9, 2.5
3'-NH 7 d 9.1
o-Ph 1 8.18 dd 8.5, 1.3
o-Ph 3 7.72 dd 8.4, 1.3
p-Ph 1 7.62 tt 7.4, 1.6
aromatic 7.45 m

Carbon NMR Peaks

Position PPM
1 79.1
2 75.3
3 40.3
4 82.1
5 82.8
6 36.1
7 75.7
8 57.6
9 207.4
10 78.1
11 133.5
12 139.7
13 72.3
14 35.3
15 42.6
16 21.2
17 25.9
18 14.7
19 16.1
20 77.6
1' 172.9
2' 73.1
3' 54.8
4-OAc C=O 172.4
4-OAc methyl 22.5
10-OAc C=O 169.5
10-OAc methyl 20.8
Ph1 C=O 167.3
q-Ph1 133.7
o-Ph1 130.3
m-Ph1 128.4
p-Ph1 133.8
q-Ph2 138.1
o-Ph2 127
m-Ph2 128.8
p-Ph2 128.9
Ph3 C=O 167.2
q-Ph3 129.4
o-Ph 3 127.1
m-Ph 3 129.1
p-Ph 3 132