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Carbohydr Res. 2006 Nov 27;341(16):2714-6. Epub 2006 Oct 2.

Direct epoxidation of D-glucal and D-galactal derivatives with in situ generated DMDO.

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  • 1Laboratorio di Chimica Organica, Dipartimento di Chimica, Universit√†, di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy.

Abstract

A multi-gram epoxidation of 3,4,6-tri-O-benzyl-D-glucal and D-galactal with dimethyldioxirane (DMDO) generated in situ from Oxone/acetone in a biphasic system (CH(2)Cl(2)-aqueous NaHCO(3)) resulted in the formation of the corresponding 1,2-anhydrosugars in a 99% yield and 100% selectivity. In a similar way, 3,4,6-tri-O-acetyl-D-glucal afforded a 7:1 mixture of the corresponding gluco and manno derivatives in an 87% overall yield.

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