Synthesis of furanoid sugar amino acids

Abstract

A novel cycloetherification process involving a facile 5-exo SN2-type ring closure by intramolecular opening of a ter- minal aziridine ring by a gamma-hydroxyl group, with concomitant debenzylation, during the deprotection of a dithioacetal moiety following a method developed by Mehta and Uma (Tetrahedron Lett., 1996, 37, 1897-1898) using nitrogen oxides, served as the key step in the stereoselective syntheses of furanoid sugar amino acids.