(+)-2α-Acetoxy-2',7-dideacetoxy-1-hydroxyaustrospicatine

(+)-2α-Acetoxy-2',7-dideacetoxy-1-hydroxyaustrospicatine

Common Name: (+)-2α-Acetoxy-2',7-dideacetoxy-1-hydroxyaustrospicatine

Synonyms: 13-​Dihydro-​2,​9,​13-​triacetyltaxine B

CAS Registry Number: 155512-17-7

InChI: InChI=1S/C39H53NO11/c1-21-29(51-31(45)19-28(40(10)11)27-15-13-12-14-16-27)17-18-38(9)33(21)35(49-25(5)43)39(46)20-30(47-23(3)41)22(2)32(37(39,7)8)34(48-24(4)42)36(38)50-26(6)44/h12-16,28-30,33-36,46H,1,17-20H2,2-11H3/t28-,29+,30+,33+,34-,35+,36+,38-,39-/m1/s1

InChIKey: InChIKey=WYAAYNQXAYRFAF-WXGAMRAUSA-N

Formula: C39H53N1O11

Molecular Weight: 711.84

Exact Mass: 711.3619

NMR Solvent: CDCl3

MHz: 600.0

Calibration: Residual solvent 7.26ppm and 77.0ppm for proton and carbon respectively.

NMR references: Doss, R.P., Carney, J.R., Shanks, Williamson, R.T., and Chamberlain, J.D. (1997). Two New Taxoids from European Yew (Taxus baccata) That Act as Pyrethroid Insecticide Synergists with the Black Vine Weevil (Otiorhynchus sulcatus)1. J. Nat. Prod. 60, 1130–1133.

Species: Taxus

Notes:

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.42 d 7
3 3.22 d 7
5 5.21 br t
6α 1.03 br d 14
6β 1.43 tt 14, 4
7α 1.32 td 13, 4
7β 1.55 br d 13
9 5.9 d 10.5
10 6 d 10.5
13 6 br t
14α 1.97 dd 15.5, 7.5
14β 2.3 dd 15.5, 9.5
16 1.66 s
17 1.2 s
18 2.12 s
19 0.82 s
20a 5.28 s
20b 4.68 s
2a' 2.83 dd 13.5, 6
2b' 3.04 dd 13.5, 9.5
3' 3.77 br t
5', 9' 7.3 m
6', 8' 7.3 m
7' 7.3 m
2-OAc 2.05 s
9-OAc 2.05 s
10-OAc 2.03 s
13-OAc 2.1 s
N-Me 2.2 br s

Carbon NMR Peaks

Position PPM
1 79.5
2 74.1
3 46.9
4 141.9
5 78
6 28.4
7 27.1
8 44.2
9 76
10 71.7
11 133.4
12 139.5
13 70.7
14 36.8
15 42.3
16 22.1
17 28.3
18 15.5
19 17.9
20 118.1
1' 170.7
2' 40.2
3' 68
4' 138.4
5', 9' 128.3
6', 8' 128.4
7' 127.4
2-OAc 171.8
2-OAc 21.2
9-OAc 170
9-OAc 20.8
10-OAc 169.8
10-OAc 21
13-OAc 170.3
13-OAc 21.3
N-Me 42.8