216578-31-3

Basic information

• Product Name: 4-[N-(tert-butoxycarbonyl)-4-methylbenzenesulfonamido]cyclopentene
• Synonyms: 4-[N-(tert-butoxycarbonyl)-4-methylbenzenesulfonamido]cyclopentene
• CAS NO: 216578-31-3
• Molecular Weight: 337.44
• Mol File: 216578-31-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-[N-(tert-butoxycarbonyl)-4-methylbenzenesulfonamido]cyclopentene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[N-(tert-butoxycarbonyl)-4-methylbenzenesulfonamido]cyclopentene(216578-31-3)
• EPA Substance Registry System: 4-[N-(tert-butoxycarbonyl)-4-methylbenzenesulfonamido]cyclopentene(216578-31-3)

Safety Data

• Hazardous Substances Data: 216578-31-3(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 70-55-3 toluene-4-sulfonamide 
• 14320-38-8 cyclopent-3-enol 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 

Relevant articles and documents

Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides

Several N-mono- and diprotected alkenes have been prepared and the stereoselectivity of their epoxidation has been investigated: N-monoprotected alkenes give cis epoxides preferentially (due to hydrogen bonding directed epoxidations) whereas N-diprotected alkenes produce trans epoxides exclusively (due to steric effects). Chiral lithium amide base-mediated rearrangement of a cis-monoprotected epoxide generated the corresponding amino-cyclopentenol in good yield and with an enantiomeric excess of 60%.

New route to 4-aminocyclopent-2-en-1-ols: Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides

A new route for the asymmetric synthesis of 4-aminocyclopent-2-en-1-ols (90% ee) for carbocyclic nucleoside analogue synthesis is described. The approach involves the stereoselective preparation of cis 4-amino-substituted cyclopentene oxides and subsequent chiral base-mediated rearrangement to the corresponding allylic alcohols. Full details on the synthesis and stereoselectivity of epoxidation of 4-amino-substituted cyclopentenes are presented. (C) 2000 Elsevier Science Ltd.