title: Direct epoxidation of D-glucal and D-galactal derivatives with in situ generated DMDO.
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.
authors.affiliation: Laboratorio di Chimica Organica, Dipartimento di Chimica, Università, di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy.
authors.forename: Pavel
authors.initials: P
authors.lastname: Cheshev
authors.forename: Alberto
authors.initials: A
authors.lastname: Marra
authors.forename: Alessandro
authors.initials: A
authors.lastname: Dondoni
mesh_terms: D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: C515780:3,4,6-tri-O-benzylglucal; D004852:Epoxy Compounds; C002038:galactal; D003847:Deoxyglucose; C064455:dimethyldioxirane; D005690:Galactose