218613-98-0

Usage

Chemical Properties

Clear Colourless Liquid

InChI:InChI=1/C17H30O3SSi/c1-15(14-20-22(5,6)17(2,3)4)12-13-21(18,19)16-10-8-7-9-11-16/h7-11,15H,12-14H2,1-6H3/t15-/m0/s1

Upstream product

• 116511-95-6 (benzenesulfonyl)methyllithium 
• 299430-30-1 (2R)-toluene-4-sulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-methylpropyl ester 
• 121587-29-9 (3S)-3-methyl-1-phenylsulfonylbutan-4-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 689220-37-9 Acetic acid (R)-2-hydroxymethyl-4-phenylsulfanyl-butyl ester 
• 105859-45-8 (S)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol 
• 263900-30-7 (-)-(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutyl phenyl sulfone 
• 128561-98-8 4-phenylthio-2-methoxycarbonyl-butanoate 

Downstream Products

• 308357-81-5 4-[(1E,3S,5Z,8R/S,10S)-3,11-bis{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole 
• 689220-38-0 ((6E,10E)-(S)-4-Benzenesulfonyl-13-furan-3-yl-2,6,10-trimethyl-trideca-6,10-dienyloxy)-tert-butyl-dimethyl-silane 
• 263900-31-8 (2S,4R,6Z,9S,10E)-1,9-Bis[(1,1-dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-4-phenylsulfonyl-2,6,10-trimethyl-undeca-6,10-diene 
• 210690-85-0 (2S,6Z,9S,10E)-1,9-Bis[(1,1-dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-2,6,10-trimethyl-undeca-6,10-diene 
• 210690-99-6 (2S,6Z,9S,10E)-9-[(1,1-Dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-2,6,10-trimethyl-undeca-6,10-dien-1-ol 
• 193146-26-8 (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid 
• 193146-63-3 (12Z,16E)-(3S,6R,7S,8S,15S)-3,7,15-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid 
• 193146-49-5 (7S,10R,11S,12S,19S,Z)-7-(tert-butyldimethylsilyloxy)-11-hydroxy-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one 
• 193146-51-9 (7S,10R,11S,12S,19S,Z)-7,11-bis(tert-butyldimethylsilyloxy)-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one 
• 193146-53-1 (5S,8R,9S,10S,17S,Z)-9-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2,2,3,3,6,6,8,10,14,19,19,20,20-tridecamethyl-17-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,18-dioxa-3,19-disilahenicos-14-en-7-one 
• 189453-10-9 epothilone D 
• 189453-35-8 (4S,7R,8S,9S,13Z,16S,1'E)-4,8-di-tert-butyldimethylsilyloxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxa-13-cyclohexadecene-2,6-dione 
• 152044-54-7 epothilone B 

Relevant academic research and scientific papers

First asymmetric synthesis of the marine furanosesterterpene natural product, (18S)-variabilin, employing enzymatic desymmetrization of propanediol derivatives

An efficient and stereodefined process is described for the first preparation of the marine furanosesterterpene tetronic acid, (18S)-variabilin, featuring lipase-catalyzed asymmetric desymmetrization of two types of propanediol precursors incorporating the terpene skeleton.

Method for producing epothilone B and derivatives, and intermediate products for this method

The invention relates to a method for producing epothilone B and derivatives, and to intermediate products for this method. According to the novel method, the epothilone B or derivatives are produced in high yields from the C1-C6, C7-C10 and C11-C20-fragm

Total Syntheses of Epothilones B and D

Total syntheses of the microtubule stabilizing antitumor drugs epothilone B and D are described, starting from optically pure (S)-malic acid and methyl (R)-3-hydroxy-2-methylpropionate. The synthesis is highly convergent by coupling the three fragments C1-C6 (fragment D), C7-C10 (fragment C), and C11-C21 (fragment B). Key steps are two stereoselective Wittig type olefinations to generate the 12,13- and 16,17-double bonds, an enantioselective Mukaiyama aldol addition to synthesize fragment D, and a sulfone anion allyl iodide alkylation to connect fragments B and C. Finally fragment D was attached to the B + C fragment via aldol addition.

Easy access to the epothilone family - Synthesis of epothilone B

An easy access to four out of five naturally occurring epothilones (A- E, 1-5) is reported. Key steps are an enantioselective Mukaiyama type aldol reaction, (E)- and (Z)-selective olefinations, and a sulfone alkylation.