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

Pavel Cheshev; Alberto Marra; Alessandro Dondoni

doi:10.1016/j.carres.2006.09.003

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

Carbohydr Res. 2006 Nov 27;341(16):2714-6. doi: 10.1016/j.carres.2006.09.003. Epub 2006 Oct 2.

Authors

Pavel Cheshev¹, Alberto Marra, Alessandro Dondoni

Affiliation

¹ Laboratorio di Chimica Organica, Dipartimento di Chimica, Università, di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy.

PMID: 17014831
DOI: 10.1016/j.carres.2006.09.003

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.

MeSH terms

Deoxyglucose / analogs & derivatives*
Deoxyglucose / chemistry
Epoxy Compounds / chemical synthesis*
Epoxy Compounds / chemistry
Galactose / analogs & derivatives*
Galactose / chemistry

Substances

3,4,6-tri-O-benzylglucal
Epoxy Compounds
galactal
Deoxyglucose
dimethyldioxirane
Galactose