Study on the synthesis of glucopyranosides

Abstract

The synthesis of glycosides has been widely explored. Recently, for the preparation of glycoside, the modified Koenigs-Knorr method is widely well used. However, the starting material, 1-halo sugars are unstable in storage. Thus we examined the preparation of glycoside from $\alpha$-D-glucose pentaacetate, instead of relatively unstable 1-halo sugar. Treatment of $\alpha$-D-glucose pentaacetate with trimethylsilyl iodide at reflux in inert solvents such as benzene or toluene, and the following addition of alcohols in situ gave $\beta$-D-glucopyranosides. The new method described herein appears to be promising for the preparation of $\beta$-D-glucopyranoside.