Synthesis of Interglycosidically<i>S</i>‐Linked 1‐Thio‐Oligosaccharides Under Microwave Irradiation

Abstract

Microwave irradiation (MWI) has accelerated the synthesis of S‐(2,3,4,6‐tetra‐O‐acetyl‐β‐D‐glucopyranosyl)thiouronium bromide (2a), whose reaction with 2,3,4,6‐tetra‐O‐acetyl‐α‐D‐glucopyranosyl bromide (1a) in the presence of Et3N afforded stereoselectively the acetylated β,β‐1‐thiotrehalose 4a. Similarly, the respective D‐galactopyranosyl 4b and 2‐acetylamino‐2‐deoxy‐D‐glucopyranosyl 4c analog as well as 4,4′‐di‐O‐(2,3,4,6‐tetra‐O‐acetyl‐β‐D‐galactopyranosyl) 4d and 4,4′‐di‐O‐(2,3,4,6‐tetra‐O‐acetyl‐α‐D‐glucopyranosyl) 4e derivatives of 2,2′,3,3′,6,6′‐hexa‐O‐acetyl β,β‐1‐thiotrehalose were prepared.