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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 6, Issue 2, 2009

Page: [106 - 109] Pages: 4

DOI: 10.2174/157017809787582843

Price: $65

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

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