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 R- and â-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 (RS,E)-2-[(2,3,4,6-tetra- O-acetyl-R-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.

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

AVERSA, Maria Chiara;BARATTUCCI, Anna;BONACCORSI, Paola Maria;GIANNETTO, Placido;
2002

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 R- and â-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 (RS,E)-2-[(2,3,4,6-tetra- O-acetyl-R-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.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11570/1580857
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