2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis

Abstract

The O-allylphenyl (AP) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions, through both direct and remote pathways. Differentiation between the two activation pathways was achieved in a mechanistic study. The orthogonal-type activation of the AP moiety along with common thioglycosides allows for the execution of efficient oligosaccharide assembly.

Keywords

• carbohydrates
• glycosylation
• leaving group
• oligosaccharides
• orthogonal strategy
• selective activation