A convenient synthesis of glycosyl chlorides from sugar hemiacetals using triphosgene as the chlorine source

R M Cicchillo; P Norris

doi:10.1016/s0008-6215(00)00115-4

A convenient synthesis of glycosyl chlorides from sugar hemiacetals using triphosgene as the chlorine source

Carbohydr Res. 2000 Sep 22;328(3):431-4. doi: 10.1016/s0008-6215(00)00115-4.

Authors

R M Cicchillo¹, P Norris

Affiliation

¹ Department of Chemistry, Youngstown State University, OH 44555-3663, USA.

PMID: 11072851
DOI: 10.1016/s0008-6215(00)00115-4

Abstract

Treating partially protected sugar hemiacetals with triphosgene in THF results in the formation of glycosyl chlorides. The method is compatible with acid-sensitive isopropylidene protecting groups in the hemiacetal substrates.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrates / chemistry*
Chlorides / chemical synthesis*
Chlorides / chemistry
Glucosides / chemical synthesis*
Glucosides / chemistry
Molecular Structure
Phosgene / analogs & derivatives*
Phosgene / chemistry*

Substances

Carbohydrates
Chlorides
Glucosides
Phosgene
bis(trichloromethyl) carbonate