De novo synthesis of 1-deoxythiosugars

• A short stereoselective synthesis of 1-deoxythiosugars is accomplished.
• Use of [BnEt3N]2MoS4 as sulfur transfer reagent and BER as reducing reagent.
• The mechanism follows nucleophilic double displacement in an intramolecular fashion.
• Efficient protecting group free synthesis of 1-deoxythiofuranoses and pyranoses.

A short and efficient chemical synthesis of biologically potent and novel 1-deoxythiosugars is accomplished. Introduction of sulfur mediated by benzyltriethylammonium tetrathiomolybdate, as a sulfur transfer reagent through nucleophilic double displacement of tosylate in α,ω-di-O-tosyl aldonolactones in an intramolecular fashion is the key feature. The subsequent reduction of thiosugar lactones with borohydride exchange resin (BER) offers a number of deoxythiosugars in good overall yield.

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