Synthesis of the ?-Rhamnopyranosides and the 6-Deoxy-?-mannoheptopyranosides

Abstract

A review is presented of the development of methods for the synthesis of ?-rhamnopyranosides and the related 6-deoxy-?-mannoheptopyranosides based on the 4,6-O-alkylidene directed synthesis of mannopyranosides and their 6-thia derivatives followed by selective reduction at the 6-position. Applications to total synthesis of complex bacterial oligosaccharides containing the title moieties are presented.

Keywords

• Desulfurization
• Glycosylation
• Oligosaccharide synthesis
• Radical reaction
• Stereoselectivity