Taxuspinanane I

Taxuspinanane I

Common Name: Taxuspinanane I

Synonyms: N-​Methyl taxol A

CAS Registry Number: 212071-25-5

InChI: InChI=1S/C48H53NO14/c1-26-32(61-44(57)37(53)36(29-17-11-8-12-18-29)49(7)42(55)30-19-13-9-14-20-30)24-48(58)41(62-43(56)31-21-15-10-16-22-31)39-46(6,33(52)23-34-47(39,25-59-34)63-28(3)51)40(54)38(60-27(2)50)35(26)45(48,4)5/h8-22,32-34,36-39,41,52-53,58H,23-25H2,1-7H3/t32-,33-,34+,36-,37+,38+,39-,41-,46+,47-,48+/m0/s1

InChIKey: InChIKey=UATZAEJDBCHOCI-JBTWBBNCSA-N

Formula: C48H53N1O14

Molecular Weight: 867.93

Exact Mass: 867.3466

NMR Solvent: CDCl3

MHz: Not clear in reference 400 or 500MHz.

Calibration: Not mentioned in reference.

NMR references: Morita, H., Gonda, A., Wei, L., Yamamura, Y., Wakabayashi, H., Takeya, K., and Itokawa, H. (1998). Taxoids from Taxus cuspidata var. nana. Phytochemistry 48, 857–862.

Species: Taxus

Notes: Numerous aromatic assignments may be interchangable, see reference for details.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.67 d 7
3 3.8 d 7
5 4.93 dd 9.4, 1.9
6α 2.54 m
6β 1.86 m
7 4.41 m
10 6.29 s
13 6.24 br t 8.2
14 2.34 m
16 1.14 s
17 1.26 s
18 1.88 s
19 1.67 s
20 4.17 d 8.3
20 4.28 d 8.3
2' 4.99 m
3' 5.88 br s
3'-Ph 7.46 m
3'-Ph 7.39 m
3'-Ph 7.39 m
5'-Ph 7.46 m
5'-Ph 7.39 m
5'-Ph 7.39 m
N-Me 2.82 br s
4-Ac 2.25 s
10-Ac 2.24 s
2-Bz 8.08 dd 7.3, 1.4
2-Bz 7.51 m
2-Bz 7.6 t 7.3
1-OH 1.89 br s
7-OH 2.43 d 4.1
2'-OH 4.32 br d 7.5

Carbon NMR Peaks

Position PPM
1 79.06
2 75.09
3 45.62
4 80.99
5 84.48
6 35.61
7 72.18
8 58.63
9 203.85
10 75.7
11 132.97
12 142.65
13 72.18
14 35.82
15 43.26
16 21.96
17 26.86
18 14.9
19 9.59
20 76.5
1' 173.53
2' 72.85
3' 61.46
4' 173.38
3'-Ph 129.08
3'-Ph 126.82
3'-Ph 130.01
3'-Ph 136.18
5'-Ph 128.65
5'-Ph 126.82
5'-Ph 128.47
5'-Ph 136.02
N-Me 37.53
4-Ac 22.34
4-Ac 170.21
10-Ac 20.88
10-Ac 171.28
2-Bz 130.21
2-Bz 128.47
2-Bz 133.64
2-Bz 129.31
2-Bz 166.9