Synthesis of glycosyl disulfides containing an α-glycosidic linkage

A wide range of symmetrical and unsymmetrical glycosyl disulfides is synthesized with focus on the use of alpha-glycosyl thiols. Oxidation of alpha-glycosyl thiols with iodine leads to symmetrical alpha,alpha-glycosyl disulfides, while unsymmetrical disulfides are readily synthesized from alpha- and beta-glycosyl thiols under the action of DDQ. Thus, glycosyl disulfides containing at least one alpha-glycosidic linkage are made available. (C) 2013 Elsevier Ltd. All rights reserved.