One‐Pot Protection Strategy of Glucosamine to Assemble Building Blocks of Chitosan and Lipid A

Abstract

This investigation describes a one‐pot reaction to prepare a series of building blocks for glycosylation reactions, such as 3‐alcohol glucosamines, fully protected glucosamines, O‐4 and O‐6 alcohol glucosamines. These reactions readily produce not only glycosyl donors and acceptors, but also different glycosyl units that can be changed based on the needs of the experiment. The synthesis of some molecules containing glucosamines, including saccharide chains of glycopeptide (GP) and precursors of lipid A disaccharide backbone, are also described. GP has good selectivity for tumor angiogenesis and this phenomenon makes the GP a potential target drug. Lipid A has recently been adopted as an adjuvant for human vaccines.