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Syntheses Of Small Cluster Oligosaccharide Mimetics, Andreas H. Franz, Paul H. Gross, Vyacheslav V. Samoshin

Andreas H. Franz

We designed multiple Small Cluster Oligosaccharide Mimetics (SCOMs) - potential glycosidase inhibitors - to be metabolically stable and small enough to enter cells or bacteria. Therefore, minimal scaffolds (urea, amide, ammonia) or simply non-glycosidic linkages of carbohydrate structures were central to our synthetic strategy, including: (a) coupling of several natural carbohydrate precursors; (b) total syntheses of aminomethyl tetrahydropyrans and their chiral amides with quinic acid; (c) glycopyranosyl cyanide reduction to prepare crowded clusters on a urea scaffold; (d) total syntheses via cycloadditions leading to amide-linked C-glycosides; (e) reduction of nitromethyl C-glycosides; and (f) a synthesis of hydroxylated 1,2- cyclohexanedicarboxylic acids.