Taxa-4(20),11-dien-2α,5α,10β-triol

Taxa-4(20),11-dien-2α,5α,10β-triol

Common Name: Taxa-4(20),11-dien-2α,5α,10β-triol

Synonyms: 2α,5α,10β-trihydroxytaxa-4(20),11(12)-diene

CAS Registry Number: 503313-16-4

InChI: InChI=1S/C20H32O3/c1-11-6-7-13-18(23)17-12(2)14(21)8-9-20(17,5)10-15(22)16(11)19(13,3)4/h13-15,17-18,21-23H,2,6-10H2,1,3-5H3/t13-,14-,15-,17-,18+,20-/m0/s1

InChIKey: InChIKey=LWVCNQGLLNEDIG-HBCJFLFASA-N

Formula: C20H32O3

Molecular Weight: 320.46

Exact Mass: 320.235145

NMR Solvent: CDCl3

MHz: 300.0

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: Relative stereochemistry not reported. Proton at position H-13 were reported as a multiplet in range of 2.50-2.30 ppm. We reported this multiplet at 2.40 ppm. Four protons at positions H-1, H-7, H-13, and H-14 reported as multiplet 2.11-1.95 ppm. We reported this multiplet as 2.03 ppm. Two protons at H-6 reported as multiplet at 1.78-1.68 ppm. We reported this multiplet at 1.73 ppm.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 2.03 m
2 4.06 br s
3 3.22 d 6.2
5 4.23 t 2.8
6 1.73 m
7 1.1 ddd 13.4, 4.7, 2.1
7 2.03 m
9 1.52 m
9 2.23 dd 14.5, 11.9
10 5.12 dd 11.7, 5.5
13 2.4 m
13 2.03 m
14 1.5 m
14 2.03 m
16 1.6 s
17 1.15 s
18 1.92 s
19 0.87 s
20 5.32 s
20 5.19 s

Carbon NMR Peaks

Position PPM
1 55.3
2 70.6
3 41.3
4 150.2
5 76.7
6 32
7 33.6
8 40.5
9 47.2
10 68.1
11 135.5
12 136.6
13 30.2
14 18.2
15 37.2
16 25.7
17 32.7
18 21.5
19 22.8
20 114.3