307494-00-4

Basic information

• Product Name: (E)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pent-2-enoic acid benzyl ester
• Synonyms: (E)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pent-2-enoic acid benzyl ester
• CAS NO: 307494-00-4
• Molecular Weight: 335.359
• Mol File: 307494-00-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pent-2-enoic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pent-2-enoic acid benzyl ester(307494-00-4)
• EPA Substance Registry System: (E)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pent-2-enoic acid benzyl ester(307494-00-4)

Safety Data

• Hazardous Substances Data: 307494-00-4(Hazardous Substances Data)

Upstream product

• 2436-29-5 3-(N-phthaloyl)propionaldehyde 
• 78385-36-1 benzyloxycarbonylmethyltriphenylphosphonium bromide 

Downstream Products

• 307494-03-7 (2S,3S)-2-Azido-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanoic acid benzyl ester 
• 307494-02-6 (2S,3S)-2-Azido-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-pentanoic acid benzyl ester 
• 307494-01-5 (2R,3S)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2,3-dihydroxy-pentanoic acid benzyl ester 

Relevant articles and documents

Thalidomide metabolites and analogs. Part 2: Cyclic derivatives of 2-N-phthalimido-2S,3S (3-hydroxy) ornithine

E-(5-N-phthaloyl)-2-pentenoic acid benzyl ester was dihydroxylated by a Sharpless AD-mix protocol followed by mononosylation of the resultant 2R,3S diol. Azide displacement of the mononosylate followed by protection with the TBDMS group gave the ε-N-phthaloyl-substituted-β-tert-butyldimethylsilyloxy-α-azidocarboxylic acid benzylester. Hydrazinolysis resulted in removal of the phthalimide group with concomitant lactamization to the 4-silyloxy-3-azidopiperidinones. Staudinger reduction of the azidopiperidinones followed by N-phthaloylation and hydrolysis of the silyl group afforded the 4'-hydroxylated-6'-deoxythalidomide derivatives. (C) 2000 Elsevier Science Ltd.