188730-08-7

Basic information

• Product Name: 4-Pentenal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methyl-5-(2-methyl-4-thiazolyl)- , (3S,4E)-
• Synonyms: (3S,4E)-3-[(tert-Butyldimethylsilyl)oxy]-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)-4-pentenal;(S,4E)-3-(tert-Butyldimethylsilyloxy)-4-methyl-5-(2-methyl-thiazol-4-yl)-pent-4-enal;(3S,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-4-methyl-5-(2-methylthiazol-4-yl)pent-4-enal;(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-(2-methyl-thiazol-4-yl)-pent-4-enal;(3S,4E)-3-(tert-Butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)-4-pentenal;(S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methylthiazol-4-yl)-pent-4-en-1-al;(3S,4E)-3-(tert-butyldimethylsilanyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)-pent-4-enal
• CAS NO: 188730-08-7
• Molecular Formula: C16H27NO2SSi
• Molecular Weight: 325.547
• Mol File: 188730-08-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-Pentenal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methyl-5-(2-methyl-4-thiazolyl)- , (3S,4E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentenal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methyl-5-(2-methyl-4-thiazolyl)- , (3S,4E)-(188730-08-7)
• EPA Substance Registry System: 4-Pentenal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methyl-5-(2-methyl-4-thiazolyl)- , (3S,4E)-(188730-08-7)

Safety Data

• Hazardous Substances Data: 188730-08-7(Hazardous Substances Data)

Upstream product

• 6436-59-5 ethyl 2-methylthiazole-4-carboxylate 

Downstream Products

• 218614-04-1 ethyl (2Z,5S,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate 
• 219989-84-1 ixabepilone 
• 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 
• 218614-16-5 (-)-(2Z,5S,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dien-1-ol 
• 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 
• 297131-81-8 (12Z,16E)-(3S,5R,6R,7S,8S,15S)-15-Acetoxy-7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dienoic acid isopropyl ester 
• 297131-79-4 Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-tridec-3-enyl ester 
• 297131-84-1 (12Z,16E)-(3S,6R,7S,8S,15S)-15-Acetoxy-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid isopropyl ester 
• 297131-83-0 (12Z,16E)-(3S,5R,6S,7S,8S,15S)-15-Acetoxy-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dienoic acid isopropyl ester 
• 297131-85-2 (12Z,16E)-(3S,6R,7S,8S,15S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid 
• 297131-86-3 (Z)-(4S,7R,8S,9S,16S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione 

Relevant articles and documents

Total syntheses of epothilones A and B via a macrolactonization-based strategy

The total syntheses of epothilones A (1) and B (2) and several analogues thereof are described. The reported strategy relies on a macrolactonization approach and features selective epoxidation of the macrocycle double bond in precursors 3 and 4 (Scheme 1), respectively, as well as high convergency and flexibility. Building blocks 9-12 and 15 were constructed by asymmetric processes and coupled via Wittig, aldol, and macrolactonization reactions to afford the basic skeleton of epothilones and that of several of their analogues by a relatively short route. The utilization ofintermediate 14, obtained via a stereoselective Wittig reaction and its Enders coupling to SAMP hydrazone 13 (Scheme 8), in combination with a stereoselective aldol reaction with the modified substrate 69 (Scheme 10) improved the stereoselectivity and efficiency of the total synthesis of these new and highly potent microtubule binding antitumor agents.