From stereocontrolled glycosylation to expeditious oligosaccharide synthesis

Abstract

This article provides an overview of chemical methods, strategies and applications that have been introduced by our group during the past decade. The major discussion point is the development of new methods for chemical glycosylation. The methods overviewed here include: new leaving and protecting groups, metal-coordination assisted synthesis, picolinyl approach to stereoselective glycosylation, etc. Also discussed is the invention of strategies for efficient oligosaccharide assembly. Innovative tools for oligosaccharide synthesis including the temporary deactivation concept, the inverse armed-disarmed strategy, thioimidateonly orthogonal and active-atent activation, and O-2/O-5 cooperative effect are discussed in light of recent results. Our recent attempts to develop new automated technologies, i.e. Surface- Tethered Iterative Carbohydrate Synthesis (STICS) and HPLCassisted oligosaccharide synthesis are also introduced. © 2013 FCCA (Forum: Carbohydrates Coming of Age).