De novo synthesis of sugar-aza-crown ethers via a domino Staudinger aza-Wittig reaction.
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.
Ménand
Mickaël
M
Synthèse, Structure et Fonction des Molécules Bioactives, CNRS UMR 7613, Université Pierre et Marie Curie, 4 Place Jussieu, F-75005 Paris, France.
Blais
Jean-Claude
JC
Valéry
Jean-Marc
JM
Xie
Juan
J
D000447:Aldehydes / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D043844:Crown Ethers / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D000447:Aldehydes; D001372:Aza Compounds; D002241:Carbohydrates; D043844:Crown Ethers