Protecting groups in carbohydrate chemistry: influence on stereoselectivity of glycosylations

Molecules. 2010 Oct 20;15(10):7235-65. doi: 10.3390/molecules15107235.

Abstract

Saccharides are polyhydroxy compounds, and their synthesis requires complex protecting group manipulations. Protecting groups are usually used to temporarily mask a functional group which may interfere with a certain reaction, but protecting groups in carbohydrate chemistry do more than protecting groups usually do. Particularly, protecting groups can participate in reactions directly or indirectly, thus affecting the stereochemical outcomes, which is important for synthesis of oligosaccharides. Herein we present an overview of recent advances in protecting groups influencing stereoselectivity in glycosylation reactions, including participating protecting groups, and conformation-constraining protecting groups in general.

Publication types

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

MeSH terms

  • Carbohydrate Conformation*
  • Carbohydrate Sequence
  • Carbohydrates / chemistry*
  • Chemistry, Organic
  • Glycosylation
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis
  • Oligosaccharides / chemistry
  • Oxazolidinones / chemistry
  • Stereoisomerism

Substances

  • Carbohydrates
  • Oligosaccharides
  • Oxazolidinones