Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite

• Glycosyl halides react efficiently with various diaryl dichalcogenides in the presence of rongalite.
• Efficient synthesis of aryl thio- and selenoglycosides is reported.
• Synthesis of peracetylated 4-methyl-7-thioumbelliferyl-β-d-cellobioside (MUS-CB) has been achieved.

A simple, mild, and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate a chalcogenide anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-β-d-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved.

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