1-Deoxy-2-deacetoxy-9-acetoxytaxine-B

1-Deoxy-2-deacetoxy-9-acetoxytaxine-B

Common Name: 1-Deoxy-2-deacetoxy-9-acetoxytaxine-B

Synonyms:

CAS Registry Number: 172303-98-9

InChI: InChI=1S/C33H45NO7/c1-18-24(36)16-22-29(38)28-19(2)25(41-26(37)17-23(34(7)8)21-12-10-9-11-13-21)14-15-33(28,6)31(40-20(3)35)30(39)27(18)32(22,4)5/h9-13,22-23,25,28-31,38-39H,2,14-17H2,1,3-8H3/t22-,23+,25-,28-,29+,30+,31-,33+/m0/s1

InChIKey: InChIKey=AKGNQELVIPFFIJ-VMJFMMKLSA-N

Formula: C33H45N1O7

Molecular Weight: 567.71

Exact Mass: 567.3196

NMR Solvent: CDCl3

MHz: 200.0

Calibration: Not mentioned

NMR references: Jenniskens, L.H.D., van Rozendaal, E.L.M., van Beek, T.A., Wiegerinck, P.H.G., and Scheeren, H.W. (1996). Identification of Six Taxine Alkaloids from Taxus baccata Needles. J. Nat. Prod. 59, 117–123.

Species: Taxus

Notes: This compound was not given a name in NMR reference. Furthermore it was misnamed in review article (Wang, Y.-F., Shi, Q.-W., Dong, M., Kiyota, H., Gu, Y.-C., and Cong, B. (2011). Natural Taxanes: Developments Since 1828. Chem. Rev. 111, 7652–7709.) as 2-deacetyl-9-acetoxytaxine B. Protons at position 6 and 7 were not observable according to literature reference. Carbon assignments for position 5 and 9 as well as 1' and acetate carboynl are reported as interchangable in reference.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 2.37 dd 6.8, 2.6
2 4.22 dd 6.4, 2.6
3 3.03 d 6.4
5 5.14 br s
9 5.66 d 9.9
10 4.97 d 9.9
14 2.5 m
14 2.61 m
16 1.73 s
17 1.24 s
18 2.15 s
19 0.9 s
20 5.35 s
20 5.38 s
2' 2.41 m
2' 2.9 m
3' 3.94 t 7.5
aromatic 7.35 m
N(CH3)2 2.25 s
9-OAc 2.09 s

Carbon NMR Peaks

Position PPM
1 51.4
2 68.1
3 44.8
4 143.3
5 78.8
6 28.6
7 27.6
8 44.5
9 77.9
10 71.5
11 155
12 134.7
13 200
14 35.7
15 37.5
16 38
17 25.4
18 14
19 17.6
20 118.4
1' 171.1
2' 38.2
3' 66.2
i-Ph 138.4
o-Ph 128.6
m-Ph 128
p-Ph 127.4
N(CH3)2 42.2
O2CMe 171.6
O2CMe 21