A tandem Ferrier and Click reaction: a facile synthesis of triazolyl-2,3-dideoxypyranosides

✍ Scribed by J.S. Yadav; B.V. Subba Reddy; D. Narasimha Chary; Ch. Suresh Reddy

• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 148 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.02.052

✦ Synopsis

Glycosyl azides, prepared in situ from glucal and trimethylsilyl azide via Ferrier rearrangement, undergo smooth coupling with alkynes under neutral conditions by means of 'Click reactions' to furnish 1,2,3-triazole-linked glycoconjugates in high yields and with moderate stereoselectivity. The method provides a convenient route to prepare glycoconjugates from glucals, trimethylsilyl azide, and alkynes via a three component reaction.