A series of sulfonium salts derived from 1,5-dithiopent-1-enopyranosides was prepared in a three-step sequence from protected D- and L-erythrofuranoses. The key step is the nucleophilic displacement of a leaving group by a sulfur atom of carbohydrate-derived ketene dithioacetals. Such compounds were assayed for their properties as glycosidase inhibitors.
Synthesis of d- and l-erythro 1,5-dithiopent-1-enopyranoside sulfonium salts and their evaluation as glycosidase inhibitors / Buchotte, Marie; Bello, Claudia; Vogel, Pierre; Floquet, Nicolas; Muzard, Murielle; Plantier-Royon, Richard. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - ELETTRONICO. - 20:(2009), pp. 2038-2042. [10.1016/j.tetasy.2009.07.033]
Synthesis of d- and l-erythro 1,5-dithiopent-1-enopyranoside sulfonium salts and their evaluation as glycosidase inhibitors
Bello, Claudia;
2009
Abstract
A series of sulfonium salts derived from 1,5-dithiopent-1-enopyranosides was prepared in a three-step sequence from protected D- and L-erythrofuranoses. The key step is the nucleophilic displacement of a leaving group by a sulfur atom of carbohydrate-derived ketene dithioacetals. Such compounds were assayed for their properties as glycosidase inhibitors.
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