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De Novo Synthesis of Sugar-Aza-Crown Ethers via a Domino Staudinger Aza-Wittig Reaction

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journal contribution
posted on 14.04.2006, 00:00 by Mickaël Ménand, Jean-Claude Blais, Jean-Marc Valéry, Juan Xie
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 α- and β-C-glycosyl azido aldehydes.