2-Amino-2-deoxy-β-mannosides, i.e., β-mannosamines, are found extensively in the capsular polysaccharides (CPS) of various harmful bacteria strains. As a class of 1,2-cis-glycosidic linkages, β-mannosamines are difficult to construct by chemical synthesis due to the steric effect and the absence of anomeric effect. Although a number of strategies have been reported, there is a lack of a direct and efficient approach for the synthesis of 2-amino-2-deoxy-β-mannosides. We have recently developed a feasible approach for stereoselective synthesis of 2-amino-2-deoxy-β-mannosides using cesium carbonate-mediated anomeric O-alkylation chemistry. In addition, this method has also been applied to the stereoselective syntheses of representative bacterial polysaccharides containing β-mannosamines. In this presentation, our recent findings in this field will be described.

Stereoselective synthesis of 2-amino-2-deoxy-β-mannosides via anomeric O-alkylation

2019 Fall National Meeting

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