Home > Organosilicon Compounds> (3S,7S,8S,12Z,15S,16E)-1,3,7,15-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one

(3S,7S,8S,12Z,15S,16E)-1,3,7,15-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one

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Origin: China

Cas No: 193146-51-9

Specification: 99%min

Min order Quantity: 1 /kg

Supply Ability: 80 mt/month

Lead time: 7 days for OEM, 3 days for ready goods

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CAS No.: 193146-51-9 Formula: C51H101NO5SSi4 Molecular Weight: 952.75800

Description

An intermediate in the synthesis of Epothilones. Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone D is in phase I clinical testing of in patients with advanced solid tumours. Epothilone D is a cytotoxic macrolide that stabilises malignant cells' microtubules and arrests mitosis, a characteristic it shares with other epothilones. They bind to the same hepatic sites as does paclitaxel (Taxol) in a 1:1 stoichiometric ratio of a, b-tubulin heterodimers.

Basic Info

Chemical Name	(3S,7S,8S,12Z,15S,16E)-1,3,7,15-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one
Synonyms	(3S,6R,7S,8S,12Z,15S,16E)-1,3,7,15-tetrakis{[tert-butyl(dimethyl)silyl]oxy}-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one; (3S,6S,7S,8S,12Z,15S,16E)-1,3,7,15-Tetra[(tert-butyldimethylsilyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-12,16-heptadecadien-5-one;
CAS No.	193146-51-9
Molecular Formula	C51H101NO5SSi4
Molecular Weight	952.75800
PSA	95.12000
LogP	16.81210

Synthesis Route

tert-Butyldimethylsilyl Trifluoromethanesulfonate+(3S,7S,8S,12Z,15S,16E)-1,3,15-tris[[tert-butyl(dimethyl)silyl]oxy]-7-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one→(3S,7S,8S,12Z,15S,16E)-1,3,7,15-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one
tert-Butyldimethylsilyl Trifluoromethanesulfonate+(3S,6S,7S,8S,12Z,15S,16E)-1,3,7-Trihydroxy-15-[(tert-butyldimethylsilyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-12,16-heptadecadien-5-one→(3S,7S,8S,12Z,15S,16E)-1,3,7,15-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one
(3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al→(3S,7S,8S,12Z,15S,16E)-1,3,7,15-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one

Precursor

(2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal
tert-Butyldimethylsilyl Trifluoromethanesulfonate
(3S,7S,8S,12Z,15S,16E)-1,3,15-tris[[tert-butyl(dimethyl)silyl]oxy]-7-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one
(3S,6S,7S,8S,12Z,15S,16E)-1,3,7-Trihydroxy-15-[(tert-butyldimethylsilyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-12,16-heptadecadien-5-one

Downstream Product

(3S,7S,8S,12Z,15S,16E)-3,7,15-tris[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid
epothilone B
epothilone D
(3S,7S,8S,12Z,15S,16E)-3,7,15-tris[[tert-butyl(dimethyl)silyl]oxy]-1-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one

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