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

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.