Multigram epoxidation of 3,4,6-tri-O-benzyl-D-glucal and D-galactal with dimethyldioxirane (DMDO) generated in situ from Oxone®/acetone in biphasic system (CH2Cl2–aqueous NaHCO3) resulted in the formation of the corresponding 1,2-anhydrosugars in 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 87% overall yield
Direct epoxidation of D-glucal and D-galactal derivatives with in situ generated DMDO
MARRA, Alberto;DONDONI, Alessandro
2006
Abstract
Multigram epoxidation of 3,4,6-tri-O-benzyl-D-glucal and D-galactal with dimethyldioxirane (DMDO) generated in situ from Oxone®/acetone in biphasic system (CH2Cl2–aqueous NaHCO3) resulted in the formation of the corresponding 1,2-anhydrosugars in 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 87% overall yieldFile in questo prodotto:
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