Taxa-4(20),11(12)-diene-5α,10β,14β-triol

Taxa-4(20),11(12)-diene-5α,10β,14β-triol

Common Name: Taxa-4(20),11(12)-diene-5α,10β,14β-triol

Synonyms: 5α,10β,14β-Trihydroxytaxa-4(20),11(12)-diene

CAS Registry Number: 503313-20-0

InChI: InChI=1S/C20H32O3/c1-11-8-16(22)14-9-13-12(2)15(21)6-7-20(13,5)10-17(23)18(11)19(14,3)4/h13-17,21-23H,2,6-10H2,1,3-5H3/t13-,14-,15+,16+,17+,20+/m1/s1

InChIKey: InChIKey=BJAFNPIVPFPJOH-QJUXXTNESA-N

Formula: C20H32O3

Molecular Weight: 320.47

Exact Mass: 320.235145

NMR Solvent: CDCl3

MHz: 400.0

Calibration: Not mentioned in literature reference.

NMR references: Horiguchi, T., Rithner, C.D., Croteau, R., and Williams, R.M. (2003). Studies on taxol biosynthesis. Preparation of 5α-acetoxytaxa-4(20),11-dien-2α,10β-diol derivatives by deoxygenation of a taxadiene tetra-acetate obtained from Japanese yew. Tetrahedron 59, 267–273.

Species: Taxus

Notes: Protons at positions 1, 2, and 6 were reported in literature as 1.61-1.49 ppm multiplet. We tabulated the chemical shift of these protons as the center of the multiplet 1.55 ppm. Hydroxyl protons at position 10 and 14 and proton at positon 7 were reported as 0.96-0.80 multiplet. We tabulated these protons at center of multiplet 0.88 ppm. Relative stereochemistry and carbon nmr assignments not reported.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 1.55 m
2 1.55 m
3 2.81 m
5 3.88 dd 3.6, 3.3
6 1.55 m
7 0.88 m
7 2.03 ddd 13, 12.8, 5.8
9 1.46 dd 14.5, 5.5
9 2.22 dd 14.5, 11.7
10 4.96 dd 11.7, 5.5
13 2.41 d 7.7
14 3.61 dd 7, 6.8
16 1.65 s
17 1.34 s
18 1.85 s
19 0.61 s
20 4.79 s
20 4.56 t 1.3
5-OH 0.58 m
10-OH 0.88 m
14-OH 0.88 m

Carbon NMR Peaks

Position PPM
156.4
140.7
133.2
108.9
74.5
71.7
68
56.5
48.5
43.1
40.1
39.2
35.6
33.9
32.6
30.9
27.4
26.8
22.2
21.5