New Oligosaccharide Analogues: Non-Glycosidically Linked Thioether­Bridged Pseudodisaccharides

The synthesis of six disaccharide analogues is reported. The pseudodisaccharides each consist of two monosaccharide residues linked non-glycosidically via a thioether functionality; both C2-symmetric and unsymmetrically substituted examples are described. The synthesis was achieved by first introducing an acetateprotected 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.