Syntheses of p-nitrophenyl 3- and 4-thio-β-D-glycopyranosides.

Thioglycosides have proved to be useful, enzymatically stable analogs of glycosides for structural and mechanistic studies and their synthesis is considerably simplified through the use of thioglycoligases. As part of an investigation into the use of thioglycosides as potential pharmacological chaperones, and as components of glycoproteins and glycolipids, the syntheses of p-nitrophenyl 3-thio-β-D-galactopyranoside, phenyl 1,4-dithio-β-D-glucopyranoside, p-nitrophenyl 4-thio-β-D-mannopyranoside and p-nitrophenyl 2-acetamido-2-deoxy-4-thio-β-D-mannopyranoside are described.