10-​Deacetyl-​10-​oxo-​7-​epi-​cephalomannine

10-​Deacetyl-​10-​oxo-​7-​epi-​cephalomannine

Common Name: 10-​Deacetyl-​10-​oxo-​7-​epi-​cephalomannine

Synonyms:

CAS Registry Number: 213276-08-5

InChI: InChI=1S/C43H49NO13/c1-8-22(2)37(50)44-31(25-15-11-9-12-16-25)33(48)39(52)55-27-20-43(53)36(56-38(51)26-17-13-10-14-18-26)34-41(7,35(49)32(47)30(23(27)3)40(43,5)6)28(46)19-29-42(34,21-54-29)57-24(4)45/h8-18,27-29,31,33-34,36,46,48,53H,19-21H2,1-7H3,(H,44,50)/b22-8+/t27-,28+,29+,31-,33+,34-,36-,41+,42-,43+/m0/s1

InChIKey: InChIKey=CBCXLNKZLIRNPI-KIAQJTORSA-N

Formula: C43H49N1O13

Molecular Weight: 787.85

Exact Mass: 787.3204

NMR Solvent: CDCl3

MHz: Not mentioned in reference

Calibration: Not mentioned in reference

NMR references: Zhang, J., Sauriol, F., Mamer, O., You, X.-L., Alaoui-Jamali, M.A., Batist, G., and Zamir, L.O. (2001). New Taxane Analogues from the Needles of Taxus canadensis. J. Nat. Prod. 64, 450–455.

Species: Taxus

Notes: Carbon assignment missing for position 10.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
OH-1 1.91 s
2 5.87 d 7.6
3 4.01 d 7.6
5 4.88 dd 8.1, 4.3
6 2.26 m
7 3.85 br ddd 11, 4.5, 2
OH-7 4.42 d 11
13 6.2 t 8.1
14a 2.45 m
14b 2.31 m
16 1.23 s
17 1.13 s
18 1.76 s
19 1.73 s
20a 4.41 d 8.6
20b 4.33 d 8.6
OAc 2.48 s
Ph-o 8.16 d 7.7
Ph-m 7.53 t 7.9
Ph-p 7.63 t 7.2
CH 2' 4.73 br t 3.1
OH 2' 3.54 d 4.1
3' 5.61 dd 9, 2.6
Ph 3' 7.35 m
NH 4' 6.44 d 8.9
Me 6' 1.78 s
Me 7' 1.71 d 6.9
CH 7' 6.42 q 6.9

Carbon NMR Peaks

Position PPM
1 78.7
2 74.9
3 39.3
4 80.9
5 82.6
6 32.2
7 77.3
8 56.3
9 206.7
11 140.7
12 142.5
13 71.8
14 36.1
15 39.7
16 25.8
17 22.5
18 14.1
19 14.9
20 77.3
OAc 22.2
OAc 171.8
OBz C=O 166.6
Ph-q 128.3
Ph-o 130.5
Ph-m 129.2
Ph-p 134
2' 73.2
3' 55.1
Ph 3' 137.6
Ph 3' 129.2
Ph 3' 126.9
Ph 3' 128.7
C=O 5' 168.9
Me 6' 12.4
6' 130.7
Me 7' 13.8
7' 132.3