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Aucagne, V ; Aversa, MC ; Barattucci, A ; Bonaccorsi, P ; Giannetto, P ; Rollin, P ; Tatibouet, A

Sulfenic acids in the carbohydrate field. Synthesis of transient glycosulfenic acids and their addition to unsaturated acceptors

Journal of Organic Chemistry 67 (20) 6925-6930

par Administrateur - publié le

Abstract :

A new method is described for building up anomeric glycosyl sulfoxides, via the formation of transient glycosulfenic acids and their addition to unsaturated acceptors. Thermolysis of alpha- and beta-3- [(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)sulfinyl]propanenitriles affords 1-glucosulfenic acids, which are reacted in situ with common substituted alkynes. The obtained (R-s,E)-2-[(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)sulfinyl] -2-butendioates are involved as enantiopure sulfinyl dienophiles in Diels-Alder reactions with 2,3-dimethyl-1,3-butadiene to evaluate the role that the sugar moiety plays in the steric control of the cycloaddition. This chemistry provides a direct synthetic strategy for the stereocontrolled connection between thioglycon and aglycon moieties, thus offering the basis for an easy elaboration of new molecules incorporating thiosugar residues.