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Synfacts 2006(7): 0740-0740  
DOI: 10.1055/s-2006-941901
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Sugar-Aza-Crown Ethers

Contributor(s): Yasuhiro Uozumi, Maki Minakawa
M. Ménand, J.-C. Blais, J.-M. Valéry, J. Xie*
Université Pierre et Marie Curie, Paris and Ecole Normale Supérieure de Cachan, France
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

A simple and efficient preparation of sugar-aza-crown (SAC) ethers is described. The key step is a domino Staudinger aza-Wittig reaction for cyclodimerization of C-glycosyl azide aldehydes 1. Treatment of 1 with polymer-bound diphenylphosphine in THF gave the cyclic imines 2 in good yields. Reduction of imines 2 led to the desired sugar-aza-crown (SAC) ethers 3 in 65-74% yield.