One-Step Synthesis of β-C-Glycosidic Ketones in Aqueous Media: The Case of 2-Acetamido Sugars

Nicolas Bragnier; Marie-Christine Scherrmann

doi:10.1055/s-2005-861816

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One-Step Synthesis of β-C-Glycosidic Ketones in Aqueous Media: The Case of 2-Acetamido Sugars

Nicolas Bragnier, Marie-Christine Scherrmann*
Laboratoire de Chimie Organique Multifonctionnelle, Bat. 420, Université de Paris XI, 91405 Orsay, France
Fax: +33(1)69154715; e-Mail: mcscherr@icmo.u-psud.fr;

Abstract

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Abstract

The one step synthesis of β-d-C-glycosidic ketones by condensation of pentane-2,4-dione with unprotected N-acetyl-d-gluco-, manno-, and galactosamine in alkaline aqueous media has been explored. N-Acetyl-d-gluco- and mannosamine gave, in good yield, a mixture of the two gluco and manno C-glycosidic ketones, which were separated by crystallization after acetylation, whereas N-acetyl-d-galactosamine afforded the galacto C-glycosidic ketone which was isolated as its acetylated derivative in 50% yield.

Key words

asymmetric synthesis - carbohydrates - condensation - C-glycosides - ketones

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