Synthesis of a library of glucal-derived triazoles via copper-catalyzed azide–alkyne cyclization

Abstract

A library of glucal-derived triazoles have been synthesized using the copper-catalyzed azide-alkyne cyclization reaction starting from 3,4,6-tri-O-acetyl-d-glucal. Different trimethylsilyl substituted alkyne derivatives of glucal were first synthesized from 3,4,6-tri-O-acetyl-d-glucal, using Sonogashira coupling, hydrostannation and iodination steps. These glucal-based trimethylsilyl-protected alkynes were then used in the copper-catalyzed cyclization reactions with different organic azides to synthesize the corresponding triazole derivatives of d-glucal.