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Aromatic O-glycosylation

På svenska

Author

Summary, in English

Carbohydrates carrying an aromatic aglycon are important natural products and thus key synthetic targets. However, due to the electron-withdrawing properties of aromatic rings, phenols are difficult to glycosylate. This review covers the most common carbohydrate donors used for aromatic O-glycosylation (anomeric acetates, halides, trichloroacetimidates and thioglycosides) as well as some less common donors. The scope of the review is to give practical examples of aromatic O-glycosylations and to offer guidelines for glycosylation of typical aromatic residues. Anomeric acetates or trichloroacetimidates, activated under acidic conditions, are preferred for electron rich aromatic aglycons, while glycosyl halides, activated using basic conditions, are preferred for electron deficient aromatic residues. (c) 2006 Elsevier Ltd. All rights reserved.

Publishing year

2006

Language

English

Pages

1266-1281

Publication/Series

Carbohydrate Research

Volume

341

Issue

10

Document type

Journal article review

Publisher

Elsevier

Topic

  • Organic Chemistry

Keywords

  • halide
  • trichloroacetimidate
  • anomeric acetate
  • glycosylation
  • aromatic

Status

Published

ISBN/ISSN/Other

  • ISSN: 1873-426X