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: ramstrom
kth.se
M. Angelin, M. Hermansson, H. Dong, O. Ramström, Eur. J. Org. Chem., 2006, 4323-4326.
DOI: 10.1002/ejoc.200600288
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.
see article for more examples
proposed mechanism
Key Words
TEMPO, Trichloroisocyanuric Acid, Aldehydes, Organocatalysis, Glycosides, Oxidation, Catalysis
ID: J24-Y2006-3150
