Efficient synthesis of 3-furanosyl-6'-furanosylphosphinate through a tandem sequential radical process

Olivier Dubert; Arnaud Gautier; Eric Condamine; Serge R Piettre

doi:10.1021/ol017011x

Efficient synthesis of 3-furanosyl-6'-furanosylphosphinate through a tandem sequential radical process

Org Lett. 2002 Feb 7;4(3):359-62. doi: 10.1021/ol017011x.

Authors

Olivier Dubert¹, Arnaud Gautier, Eric Condamine, Serge R Piettre

Affiliation

¹ Laboratoire des Fonctions Azotées et Oxygénées Complexes, UMR 6014 CNRS, Université de Rouen, IRCOF, Rue Tesnière, F-76821 Mont Saint Aignan, France.

PMID: 11820879
DOI: 10.1021/ol017011x

Abstract

The sodium salt of hypophosphorous acid is shown to act as a double radical precursor in a double, sequential radical addition on 3-exo-methylenefuranose derivative 14 and 4-ethylenefuranose 10 to furnish phosphinates 18d in good overall yields. Unambiguous structural assignment establishes the high diastereoselection of the process.