ABSTRACT
The propargyl function in organic synthesis in general and in carbohydrate chemistry in particular is a well-established dipolarophile component in 1,3-dipolar cycloaddition reaction for the synthesis of different triazole or isoxazole derivatives. Another useful application of propargyl glucopyranoside has been reported in a one-pot three-component reaction of alkyne-aldehyde-aniline for the successful construction of quinoline-based glycoconjugates. The chapter describes a more detailed protocol for the synthesis of 2,3,4,6-tetra-O-acetyl-ß-d-glucopyranoside 2 than that described, from 1,2,3,4,6-penta-O-acetyl-ß-d-glucopyranose 1 and propargyl alcohol in the presence of boron trifluoride etherate. The reaction was performed using commercial reagents and solvents purified prior to use according to standard procedures. Reactions were monitored by TLC.
