Abstract

The synthesis of C2-symmetric glycophanes incorporating two triazole linkers has been achieved in seven steps from 3,4,6-tri-O-acetyl-D-glucal in good overall yields. The intermolecular Cu(I)-mediated Huisgen reaction was used for the ring closure key-step to give almost exclusively 24-, 26-, and 32-membered chiral macrocycles without significant polymerization. Target compounds however had low solubility in water, precluding investigation of their recognition behaviour in this medium.

Keywords: carbohydrate, Ferrier reaction, Huisgen cycloaddition, click chemistry, glycophane