Automated Solution-Phase Synthesis of S-Glycosides for the Production of Oligomannopyranoside Derivatives.

Thioglycosides are more resistant to enzymatic hydrolysis than their O-linked counterparts, thereby becoming attractive targets for carbohydrate-based therapeutic development. We report the first development of methods for the site-selective incorporation of S-linkages into automated solution-phase oligosaccharide protocols. The protocols were shown to be compatible with the formation of S- or O-glycosides for the synthesis of mannopyranoside trimmers that incorporate both S- and O-linkages to allow the selective incorporation of an S-glycoside in various stages in an automated program.