2α,5α,9α,10β-tetraacetoxy-13α-(Z)-cinnamoyloxy-taxa-4(20),11-diene

2α,5α,9α,10β-tetraacetoxy-13α-(Z)-cinnamoyloxy-taxa-4(20),11-diene

Common Name: 2α,5α,9α,10β-tetraacetoxy-13α-(Z)-cinnamoyloxy-taxa-4(20),11-diene

Synonyms:

CAS Registry Number: 587888-11-7

InChI: InChI=1S/C37H46O10/c1-20-28(43-22(3)38)17-18-37(9)32(20)33(44-23(4)39)27-19-29(47-30(42)16-15-26-13-11-10-12-14-26)21(2)31(36(27,7)8)34(45-24(5)40)35(37)46-25(6)41/h10-16,27-29,32-35H,1,17-19H2,2-9H3/b16-15-/t27-,28-,29-,32-,33+,34+,35-,37+/m0/s1

InChIKey: InChIKey=VPIDEXLSMIAAAD-BUVRCVSPSA-N

Formula: C37H46O10

Molecular Weight: 650.76

Exact Mass: 650.3091

NMR Solvent: CDCl3

MHz: 500.0

Calibration: Not specified in paper.

NMR references: Shi, Q.-W., Petzke, T.L., Sauriol, F., Mamer, O., and Zamir, L.O. (2003). Taxanes in rooted cuttings vs. mature Japanese yew. Canadian Journal of Chemistry 81, 64–74.

Species: Taxus

Notes: Relative stereochemistry missing for protons at positions 6 and 7. Coupling constant for proton at positions 14a missing. Carbon signals for positions 4, 14, and 1' are missing.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 1.94 br d 9.1
2 5.48 dd 6.9, 2.2
3 3.32 d 6.9
5 5.34 m
6 1.89 m
6 1.7 m
7 1.8 m
8 1.71 m
9 5.93 d 10.5
10 6.02 d 10.5
13 5.89 br t
14a 2.6 dt
14b 1.54 m
16 1.13 s
17 1.76 s
18 2.17 br s
19 0.89 s
20a 5.35 s
20b 4.81 s
OAc 2.18 s
OAc 2.04 s
OAc 2.02 s
OAc 2 s
2' 6.26 d 12.7
3' 6.96 d 12.7
Ph' o 7.47 dd 8, 2.1
Ph' m 7.36 m
Ph' p 7.36 m

Carbon NMR Peaks

Position PPM
1 47.8
2 71.2
3 43.3
5 77.6
6 28.5
7 27.3
8 44.1
9 75.9
10 71.6
11 133.3
12 137.4
13 69.5
15 37.5
16 30.7
17 26.2
18 14.5
19 17.3
20 117.4
OAc 20.8
OAc 20.1
OAc 20.7
OAc 20.3
OAc 170.5
OAc 170
OAc 169.6
OAc 170
2' 119
3' 143.9
Ph' o 129.5
Ph' m 127.4
Ph' p 128.8