4-Hydroxymethyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole

Abstract

The structure of the title compound, C₁₇H₂₃N₃O₁₀, (2), has been determined as part of our investigation into the synthetic utility of the glucosyl triazole unit in carbohydrate chemistry. Compound (2) was synthesized by the 1,3-dipolar cyclo­addition reaction of propargyl alcohol with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide under conditions which afforded (2) exclusively with complete retention of anomeric stereochemistry. The six-membered carbohydrate ring adopts a chair conformation. The non-H substituents are located in equatorial positions.