Abstract
Four chain-extended analogues of the naturally occurring glycosidase inhibitor salacinol were synthesized for structureactivity studies with different glycosidase enzymes. The syntheses involved the reaction of isopropylidene-protected 1,4-thio- and 1,4-seleno-D-talitols and 1,5-thio- and 1,5-seleno-L-gulitols, derived from D-mannose, with a benzylidene- and isopropylidene-protected 1,3-cyclic sulfate, also derived from D-mannose. Deprotection of the products afforded the novel selenonium and sulfonium sulfates composed of heterocyclic five- and six-membered ring core structures with pendant polyhydroxylated, acyclic chains of six carbon atoms.Key words: glycosidase inhibitors, zwitterionic selenonium and sulfonium sulfates, cyclic sulfate
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