para-Chlorophenyl Carbonate as a Versatile Hydroxyl Protecting Group

Kerry Routenberg Love; Peter H. Seeberger

doi:10.1055/s-2001-10797

Synthesis 2001; 2001(2): 0317-0322
DOI: 10.1055/s-2001-10797

paper

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para-Chlorophenyl Carbonate as a Versatile Hydroxyl Protecting Group

Kerry Routenberg Love^* , Peter H. Seeberger

^*Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA 02139, USA; Fax +1(617)2537929; E-mail: seeberg§mit.edu

Abstract

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The p-chlorophenyl carbonate (CPC) group can be readily applied and rapidly removed in the presence of various protecting groups including pivaloyl and benzoyl esters. Additionally, the CPC group is stable under a variety of glycosylation conditions and yields solely β-linked glycosides when used as a C2 participating group.

protecting groups - oligosaccharides - glycosylations - carbonates - participating groups - deprotection - carbohydrates

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