381 Synthesis and Characterization of Small Cluster Oligosaccharide Mimetics

Friday, November 6, 2009: 1:30 PM
Angus (Camino Real Hotel)
Andreas Franz , Department of Chemistry, University of the Pacific, Stockton, CA
Paul H. Gross , Department of Chemistry, University of the Pacific, Stockton, CA
Vyacheslav V. Samoshin , Department of Chemistry, University of the Pacific, Stockton, CA
C-Glycosides are known for interesting biological activities and have become attractive targets for synthesis and structure elucidation. The synthesis of C-C-linked oligosaccharide mimetics from Ferrier-dimerization is discussed. Detailed NMR analysis revealed a standard set of coupling constants for 2,3-enopyranosyl ring systems free of conformational averaging. In addition, quinic amide sugar mimetics were found to have an unusual twist-boat conformation in solution, which appeared to be independent from substituents and may be a consequence of ring strain.