274908-76-8

Basic information

• Product Name: Ethyl (E)-4-[tert-butyl(diphenyl)siloxy]-3-{[(trifluoromethyl)sulfonyl]oxy}but-2-enoate
• Synonyms: Ethyl (E)-4-[tert-butyl(diphenyl)siloxy]-3-{[(trifluoromethyl)sulfonyl]oxy}but-2-enoate
• CAS NO: 274908-76-8
• Molecular Weight: 516.61
• Mol File: 274908-76-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Ethyl (E)-4-[tert-butyl(diphenyl)siloxy]-3-{[(trifluoromethyl)sulfonyl]oxy}but-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl (E)-4-[tert-butyl(diphenyl)siloxy]-3-{[(trifluoromethyl)sulfonyl]oxy}but-2-enoate(274908-76-8)
• EPA Substance Registry System: Ethyl (E)-4-[tert-butyl(diphenyl)siloxy]-3-{[(trifluoromethyl)sulfonyl]oxy}but-2-enoate(274908-76-8)

Safety Data

• Hazardous Substances Data: 274908-76-8(Hazardous Substances Data)

Upstream product

• 145100-50-1 1,1,1-trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methane sulfonamide 
• 274908-66-6 Ethyl (Z)-4-[tert-Butyl(diphenyl)siloxy]-3-oxobutanoate 
• 115869-43-7 (tert-butyldiphenylsilanyloxy)acetaldehyde 
• 274908-65-5 Ethyl 2-(tert-butyldiphenylsiloxy)-3-hydroxybutanoate 
• 136787-49-0 3-(tert-butyldiphenylsilyloxy)prop-1-ene 

Relevant articles and documents

β-alkoxycarbonyl enol triflates as precursors of stereopure 3-ene-1,5- diyne building blocks for the chromophores of neocarzinostatin, C-1027, kedarcidin, maduropeptin, and N1999A2

A 5-step synthesis of α-alkoxymethyl-, α-siloxymethyl-and α- (carbamoyloxy)methyl-substituted enediynes 7 from type 23 β-oxo esters was developed following the strategy of Scheme 2. Specifically, the β-oxo esters 33, 36 and 38 (prepared as shown in Scheme 4) and NaH (or t-BuLi) gave Z- enolates in THF and E-enolates in DMF which were scavenged as enol triflates Z-27a-c and E-27a-c, respectively, upon treatment with triflimides 40 or 41 (Scheme 5). The Z-configurated enol triflates underwent Cacchi couplings with (trimethylsilyl)acetylene to give the pent-2-en-4-yne-1-carboxylates E-42a-c (Scheme 5). These were reduced to the corresponding aldehydes E-44a-c (Scheme 6) which were homologated with lithio(trimethylsilyl)diazomethane to furnish the desired enediynes 45a-c as pure E-isomers.