Direct, Mild, and Selective Synthesis of Unprotected Dialdo‐Glycosides

Abstract

Abstract A direct and highly convenient organocatalytic method for the preparation of 1,5‐dialdo‐pyranosides and 1,4‐dialdo‐furanosides is presented. The method relies on the chemoselective properties of TEMPO in combination with trichloroisocyanuric acid under very mild, basic conditions. Unprotected glycosides are prepared in a single step in high yields and are efficiently purified with the use of solid‐phase imine capture. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)