Syntheses of small cluster oligosaccharide mimeticsARKIVOC
AbstractWe 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.
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Citation InformationAndreas H. Franz, Paul H. Gross and Vyacheslav V. Samoshin. "Syntheses of small cluster oligosaccharide mimetics" ARKIVOC Vol. 2008 Iss. 1 (2008) p. 231 - 308 ISSN: 1551-7012
Available at: http://works.bepress.com/andreas-franz/60/