De novo synthesis of sugar-aza-crown ethers via a domino Staudinger aza-Wittig reaction.

J Org Chem

Synthèse, Structure et Fonction des Molécules Bioactives, CNRS UMR 7613, Université Pierre et Marie Curie, 4 Place Jussieu, F-75005 Paris, France.

Published: April 2006

A short and highly efficient route to sugar-aza-crown (SAC) ethers has been developed. The key step of the transformation is a one-pot cyclodimerization of C-glycosyl azido aldehydes via a domino Staudinger aza-Wittig reaction. This process allows the preparation of various orthogonally protected SAC ethers, from both alpha- and beta-C-glycosyl azido aldehydes.

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http://dx.doi.org/10.1021/jo052489qDOI Listing

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