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

…, M Hermansson, H Dong, O Ramström

Index: Angelin, Marcus; Hermansson, Magnus; Dong, Hai; Ramstrom, Olof European Journal of Organic Chemistry, 2006 , # 19 p. 4323 - 4326

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Citation Number: 21

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 ...