10β-Deacetylbaccatin III

10β-Deacetylbaccatin III

Common Name: 10β-Deacetylbaccatin III

Synonyms: Tax-11-en-9-one, 5β,20-epoxy-1,2α,4,7β,10β,13α-hexahydroxy-, 4-acetate 2-benzoate

CAS Registry Number: 32981-86-5

InChI: InChI=1S/C29H36O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,17-19,21-22,24,31-33,36H,11-13H2,1-5H3/t17-,18-,19+,21+,22-,24-,27+,28-,29+/m0/s1

InChIKey: InChIKey=YWLXLRUDGLRYDR-ZHPRIASZSA-N

Formula: C29H36O10

Molecular Weight: 544.591

Exact Mass: 544.2308

NMR Solvent: CDCl3

MHz: 500.0

Calibration:

NMR references: Arnone, A., Bava, A., Fronza, G., and Nasini, G. (2009). Anomalous Microbial Transformations on the Taxane Ring of 10-DAB by a Strain of the Fungus Curvularia lunata: Transbenzoylation, Transacetylation, and Opening of the Oxetane Ring. J. Nat. Prod. 72, 2000–2004.

Species: Taxus

Notes: Kingston, D.G.I., Hawkins, D.R., and Ovington, L. (1982). New Taxanes From Taxus brevifolia. J. Nat. Prod. 45, 466–470 reported first isolation from a taxus species while Arnone et al., 2009 provides complete proton and carbon NMR data.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.65 ddd 7.2, 1.2
3 4.04 d 7.2
5 4.97 dddd 9.6, 2.2, 1.1, 1.1
6a 2.45 ddd 14.3, 9.6, 6.9
6b 1.83 ddd 14.3, 11.1, 2.2
7 4.35 ddd 11.1, 7.4, 6.9
10 5.27 d 2.3
13 4.91 dddq 9.2, 7.3, 4.7, 1.4
14a 2.47 dd 15.6, 7.3
14b 2.33 ddd 15.6, 9.2, 1.2
16 1.09 s
17 1.11 s
18 2.06 d 1.4
19 1.72 s
20a 4.18 dd 8.1, 1.1
20b 4.17 dd 8.1, 1.1
OH-1 3.4 s
OBz 8.11 m
OBz 7.65 m
OBz 7.54 m
OR-4(OAC) 2.26 s
OR-7(OH) 4.12 d 7.4
OR-10(OH) 4.22 d 2.3
OR-13(OH) 4.53 d 4.7

Carbon NMR Peaks

Position PPM
1 79
2 75.2
3 47
4 81
5 84.2
6 37.2
7 72.2
8 57.9
9 211.9
10 75
11 135.2
12 142.3
13 68.1
14 38.9
15 42.8
16 26.8
17 19.8
18 15.1
19 9.8
20 77.3
OBz 167.2
OBz 133.7
OBz 130.2
OBz 129.6
OBz 128.7
OAc-4 qC 170.8
Oac-4 CH3 22.7