Reactions of sugar 1-carbonates with sugar derivatives bearing a hydroxy-group; novel method for preparation of orthoesters combining two monosaccharide units, and disaccharides

Abstract

2,3,4,6-Tetra-O-acetyl-β-D-glucopyranose 1-carbonates (1) and (4) react with 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose (2) to give 3,4,6-tri-O-acetyl-α-D-glucopyranose 1,2-(1,2,3,4-tetra-O-acetyl-6-deoxy-β-D-glucopyranos-6-anyl)orthoacetate whereas 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 1-carbonates (7) and (8) react with (2) to afford 1,2,3,4-tetra-O-acetyl-6-O-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)-β-D-glucopyranose (9).