3-Aminodeoxypyranoses in Glycosylation: Diversity-Oriented Synthesis and Assembly in Oligosaccharides

Angew Chem Int Ed Engl. 2017 May 2;56(19):5227-5231. doi: 10.1002/anie.201700178. Epub 2017 Mar 20.

Abstract

A concise, diversity-oriented approach for the synthesis of naturally occurring 3-amino- and 3-nitro-2,3,6-trideoxypyranose derivatives and analogues thereof from simple sugars has been developed. In addition, we investigated the synthesis of various 3-aminoglycosyl donors and their application in glycosylation reactions. These studies led to the successful synthesis of a tetrasaccharide containing four different 3-aminosugar components using ortho-alkynylbenzoate donors.

Keywords: 3-aminosugars; 3-nitrosugars; glycosylation; oligosaccharides; synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Sugars / chemistry*
  • Glycosylation
  • Molecular Structure
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry

Substances

  • Amino Sugars
  • Oligosaccharides