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

Marcus Angelin, Magnus Hermansson, Hai Dong, Olof Ramström*

*KTH - Royal Institute of Technology, Department of Chemistry, Teknikringen 30, 10044 Stockholm, Sweden, Email: ramstromkth.se

M. Angelin, M. Hermansson, H. Dong, O. Ramström, Eur. J. Org. Chem., 2006, 4323-4326.

DOI: 10.1002/ejoc.200600288 (free Supporting Information)


Abstract

A highly convenient organocatalytic method for the mono-oxidation of unprotected glycosides relies on the chemoselective properties of TEMPO in combination with trichloroisocyanuric acid under very mild, basic conditions. The resulting dialdo-glycosides are efficiently purified with the use of solid-phase imine capture.

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proposed mechanism



Key Words

TEMPO, Trichloroisocyanuric Acid, Aldehydes, Organocatalysis, Glycosides, Oxidation, Catalysis


ID: J24-Y2006-3150