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First synthesis of P-aryl-phosphinosugars, organophosphorus analogues of C-arylglycosides
Journal article   Peer reviewed

First synthesis of P-aryl-phosphinosugars, organophosphorus analogues of C-arylglycosides

Henri-Jean Cristau, Jérôme Monbrun, Julie Schleiss, David Virieux and Jean-Luc Pirat
Tetrahedron Letters, Vol.46
21/03/2005

Abstract

Phostone Sugar analogues Arylphosphinic Polyhydroxylated. Polyhydroxylated
The synthesis and X-ray crystal structure of the first example of arylphosphinosugar are reported. The protected polyhydroxylated 1,2-oxaphosphinane is prepared by a two steps sequence (phenylphosphinate addition on protected mannofuranose followed by intramolecular transesterification) on gram scale. Deprotection of the di-isopropylidene derivative using acidic cation-exchange resin affords the free hydroxy organophosphorus heterocycle analogous to C-arylglycosides.
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