10-(β-Hydroxybutyrl)-10-deacetylbaccaatin III

10-(β-Hydroxybutyrl)-10-deacetylbaccaatin III

Common Name: 10-(β-Hydroxybutyrl)-10-deacetylbaccaatin III

Synonyms: 10-deacetyl-10-(β-hydroxybutyryl)baccatin I

CAS Registry Number: 205674-66-4

InChI: InChI=1S/C33H44O11/c1-17(34)12-24(38)43-26-25-18(2)21(36)14-33(40,30(25,4)5)29(41-15-20-10-8-7-9-11-20)27-31(6,28(26)39)22(37)13-23-32(27,16-42-23)44-19(3)35/h7-11,17,21-23,26-27,29,34,36-37,40H,12-16H2,1-6H3/t17?,21-,22-,23+,26+,27-,29-,31+,32-,33+/m0/s1

InChIKey: InChIKey=ZBGABQBWQPLRCP-UBBNWKECSA-N

Formula: C33H44O11

Molecular Weight: 616.7

Exact Mass: 616.2884

NMR Solvent: CDCl3

MHz: 500.0

Calibration: TMS

NMR references: Soto, J., and Castedo, L. (1998). Taxoids from european yew, Taxus baccata L. Phytochemistry 47, 817–819.

Species: Taxus

Notes: Coupling constants don't seem to have been calculated accurately (nearest 0.5 Hz). Relative stereochemistry not reported for protons at position 6.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.58 d 7
3 3.82 d 7
5 4.95 dd 9.5, 2
6 2.6 m
6 1.8 m
7 4.39 dd 11, 7
10 6.4 s
13 4.79 br t
14 2.4 m
16 1.07 s
17 1.05 s
18 2.02 s
19 1.65 s
20 4.26 d 8.5
20 4.12 d 8.5
Ph (o) 8.1 d 7.5
Ph (m) 7.48 t 7.5
Ph (p) 7.6 t 7.5
2' 2.6 m
2' 2.74 dd 16, 4
3' 4.33 m
4' 1.29 d 6
Ac 2.28 s

Carbon NMR Peaks

Position PPM
1 79.3
2 75.5
3 47.3
4 81.3
5 85.1
6 36.1
7 72.2
8 59
9 205.3
10 76.6
11 131.5
12 147.8
13 67.7
14 39.3
15 43.2
16 21.4
17 27.2
18 15.8
19 10.1
20 76.8
PhCO 167.5
Ph (i) 129.74
Ph (o) 129.02
Ph (m) 130.3
Ph (p) 134.2
1' 170.8
2' 44.4
3' 65
4' 22.2
Ac 22.9
Ac 171.5