Protecting-group- and microwave-free synthesis of β-glycosyl esters and aryl β-glycosides of N-acetyl-d-glucosamine

Abstract

A protecting-group-free method for synthesis of β-glycosyl esters and aryl β-glycosides was developed by using latent chemical reactivity of N-acetyl-d-glucosamine (GlcNAc) oxazoline. The GlcNAc oxazoline was spontaneously reacted with carboxylic acids and phenol derivatives via the oxazoline ring opening without the use of a catalyst or heating conditions (i.e., microwave irradiation), affording the desired products in moderate to excellent yields with β-selectivity. This simple protecting-group-free method exhibits a wide substrate scope and good functional group tolerance, and it allows the efficient production of a novel class of GlcNAc-conjugated biomaterials and prodrug candidates.

Keywords: Aryl β-glycosides; N-acetyl-d-glucosamine oxazoline; Oxazoline ring opening; Protecting-group-free synthesis; β-glycosyl esters.