Peptidyl Carbamates: Efficient Synthesis UsingN-Fmoc-β-aminoalkoxy Carbonyl Chlorides/Active Pentachlorophenyl Carbonates as Monomeric Building Blocks

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Abstract

A simple protocol for the synthesis of linear peptidylcarbamates employing Fmoc-β-aminoalkoxy carbonyl chlorides is described. The N-Fmoc-β-aminoalkoxy carbonyl chlorides were prepared by the reaction of phosgene or triphosgene with Fmoc-protected β-amino alcohol which were isolated as solids. These oxycarbonyl chlorides were also converted to the corresponding pentachlorophenyl carbonates by reacting with pentachlorophenol. Fmoc-β-aminoalkoxy carbonyl chlorides as well as pentachlorophenol carbonates were successfully used as monomeric building blocks for the synthesis of several peptidyl carbamates.

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