β-Mannosides are critical components of a wide range of biologically significant molecules including N-linked glycans, bacterial capsular polysaccharides, fungal metabolites, and glycolipids. Although remarkable success has been achieved, stereoselective synthesis of β-mannosides remains challenging due to steric effect of the axial C2-substituent as well as the absence of anomeric effect and neighboring group participation. Recently, we developed a new method for stereoselective β-mannosylation via cesium carbonate-mediated anomeric O-alkylation. In this presentation, we will describe our recent efforts in mechanistic studies of this reaction as well as its application to the synthesis of complex carbohydrate molecules.

Stereoselective β-Mannosylation via Cs2CO3-mediated anomeric O-alkylation: Mechanistic investigations and syntheses of complex carbohydrate molecules

2019 Spring National Meeting

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