Elaboration of a novel type of interglycosidic linkage: syntheses of disulfide disaccharides

Asymmetric non-reducing disaccharides containing an interglycosidic disulfide linkage were synthesised under mild conditions through reaction of tetraacetyl-β-d-glucopyranosyl methanethiolsulfonate with O-acetylated 1-thio-aldopyranoses. The preferred conformation around the SS bond is close to that observed in unconstrained disulfides (−90°).