Synthesis of C2-symmetric Glycophanes Through a ‘Click Chemistry’ Approach

Title: Synthesis of C2-symmetric Glycophanes Through a ‘Click Chemistry’ Approach

Volume: 6 Issue: 2

Author(s): Gildas R. Balou, Jean-Pierre Joly, Lionel Vernex-Loset and Yves Chapleur

Affiliation:

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

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.

Cite this article as:

Balou R. Gildas, Joly Jean-Pierre, Vernex-Loset Lionel and Chapleur Yves, Synthesis of C2-symmetric Glycophanes Through a ‘Click Chemistry’ Approach, Letters in Organic Chemistry 2009; 6 (2) . https://dx.doi.org/10.2174/157017809787582843