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