Stereoselective Synthesis of Mixed Acetal Glycosides by Reaction of Tri-O-acetyl-N-(2,4-dinitrophenyl)-α-D-glucosaminyl Bromide with Alcohol in Acetone

Article abstract of DOI:10.1246/bcsj.55.3665

Some mixed acetal glycosides were stereoselectively synthesized by the reaction of 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl bromide with alcohols in acetone containing Hg(CN)2, HgBr2, and tetrabutylammonium bromide at room temperature.When t-butyl alcohol was used, a novel enol glycoside of acetone was formed.