We have developed new approach for the effective synthesis of 1,2-cis-2-aminosugars via nickel-catalyzed alpha-selective glycosylation with C(2)-N-substituted benzylideneamino trihaloacetimidate donors. These aminosugars make up one of the most important classes of oligosaccharides and glycoconjugates. In general, obtaining an adequate supply of these sugars from natural sources is exceedingly challenging. In many cases, high purity 1,2-cis-2-aminosugars can only be obtained by chemical synthesis. Even though there have been remarkable advances in the synthesis of 1,2-cis-2-amino glycosides, the disadvantages of current methods include the use of excess activating agents and unpredictable/poor anomeric selectivity.Our approach to glycosylation forming aminosugar molecules is innovative in that we apply modern organometallic methodology to solve issues of yield and selectivity that cannot be achieved under the current state-of-the-art methods. Our approach relies on the nickel-ligand complex and the nature of metal-bound functional groups at the C(1)- and C(2)-position on glycosyl donors to control the alpha-selectivity. Our methods are broadly applicable and provide highly-yielding and selective products. The efficacy of our transition-metal catalyzed glycosylation method is being applied to the synthesis of heparin oligosaccharides. The development of the nickel-catalyzed selective glycosylation method and the synthesis and biological studies of heparin oligosaccharides will be presented at this conference.

Approaches to 1,2-<i>cis</i>-2-amino glycosides via transition metal catalysis and application to the synthesis of heparin oligosaccharides

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.

Approaches to 1,2-cis-2-amino glycosides via transition metal catalysis and application to the synthesis of heparin oligosaccharides