9-Deacetyltaxinine E

9-Deacetyltaxinine E

Common Name: 9-Deacetyltaxinine E

Synonyms:

CAS Registry Number: 284672-78-2

InChI: InChI=1S/C35H44O9/c1-19-26(44-28(39)15-14-24-12-10-9-11-13-24)16-17-35(8)30(19)31(42-22(4)37)25-18-27(41-21(3)36)20(2)29(34(25,6)7)32(33(35)40)43-23(5)38/h9-15,25-27,30-33,40H,1,16-18H2,2-8H3/b15-14+/t25-,26-,27-,30-,31+,32+,33-,35+/m0/s1

InChIKey: InChIKey=MNKBCBWUAFDXSP-JVJUJCKXSA-N

Formula: C35H44O9

Molecular Weight: 608.72

Exact Mass: 608.2985

NMR Solvent: CDCl3

MHz: 500.0

Calibration: Solvent residue 7.25 ppm for proton and 77.0 ppm for carbon.

NMR references: Zhang, J., Sauriol, F., Mamer, O., and Zamir, L.O. (2000). New Taxanes from the Needles of Taxus canadensis. J. Nat. Prod. 63, 929–933.

Species: Taxus

Notes: Chemical shift assignment not clear in reference for CH=β OCinn. Possible type error, see reference. Proton at 1.82 ppm (br d) was unassigned in literature however by process of elimination and likely position it should be assigned to position 1, which we report in our table. Carbons at 19 was assigned twice while carbon 18 was unassigned (15.2 and 18.2 ppm). Chemical shift (ppm) values were put in our table however we left out positional assignment. Carbon 4 ppm assignment is also missing.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 1.82 br d 8.8
2 5.42 dd 6, 1.9
3 3.34 d 6
5 5.47 t 3
6a 1.86 m
6b 1.73 m
7a 1.97 m
7b 1.66 m
9 4.34 dd 9.7, 2.4
10 5.86 d 9.7
13 5.78 br t 8
14a 2.65 m
14b 1.47 dd 15.3, 7.6
16 1.1 s
17 1.62 s
18 2.31 s
19 1.1 s
20a 5.38 s
20b 5.01 s
Ph-m OCinn 7.49 m
Ph-m, p-OCinn 7.4 m
CH=α OCinn 6.67 d 16
OH-9 2.17 m
OCOCH3 2.11 s
OCOCH3 2.03 s
OCOCH3 1.79 s

Carbon NMR Peaks

Position PPM
1 47.9
2 72.2
3 43.7
5 78.8
6 28.7
7 25.7
8 44.2
9 75.8
10 75.6
11 134
12 136.4
13 70.2
14 28.4
15 37.3
16 31.4
17 27.1
18.2
15.2
20 117.7
OCOCH3 170.4
OCOCH3 170
OCOCH3 169.2
OCinn 166
CH=β OCinn 145
Ph-1 OCinn 134.1
Ph-p OCinn 130.4
Ph-m OCinn 129.1
Ph-o OCinn 127.9
CH=α OCinn 118.7
OCOCH3 21.5
OCOCH3 21.4
OCOCH3 21