New Oligosaccharide Analogues: Non-Glycosidically Linked Thioether-­Bridged Pseudodisaccharides

Abstract

The synthesis of six disaccharide analogues is reported. The pseudodisaccharides each consist of two monosaccharide residues linked non-glycosidically via a thioether functionality; both C 2-symmetric and unsymmetrically substituted examples are described. The synthesis was achieved by first introducing an acetate-protected sulfur into partially protected carbohydrates by SN2 displacement of sulfonate esters by thioacetate. Deacetylation of the sulfur was followed by treatment with another carbohydrate sulfonate derivative, and a second SN2 displacement gave the pseudodisaccharide products.