Synthesis of novel glycolipids derived from glycopyranosyl azides and N-(β-glycopyranosyl)azidoacetamides

A general and expedient method based on a click reaction has been developed for the synthesis of novel glycolipids. The Cu(I) catalyzed [3+2] cycloaddition of several fully acetylated β- as well as α-d-glycopyranosyl azides, including the 1,6-diazide derived from d-glucose, with long chain alkyl pro...

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Bibliographic Details
Published in:Tetrahedron letters 2008-10, Vol.49 (44), p.6356-6359
Main Authors: Paul, Katuri J.V., Loganathan, Duraikkannu
Format: Article
Language:English
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Summary:A general and expedient method based on a click reaction has been developed for the synthesis of novel glycolipids. The Cu(I) catalyzed [3+2] cycloaddition of several fully acetylated β- as well as α-d-glycopyranosyl azides, including the 1,6-diazide derived from d-glucose, with long chain alkyl propargyl ethers gave the respective 1,4-substituted 1,2,3-triazole derivatives in good yields. Treatment of fully acetylated N-(β-glycopyranosyl)azidoacetamides under similar conditions with alkyl propargyl ethers afforded the 1,2,3-triazolylacetamido derivatives in fairly good yields. Zemplen de-O-acetylation of all the fully acetylated derivatives furnished the free glycolipids in quantitative yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.08.073