Oligosaccharides and glycoconjugates play essential roles in numerous important biological processes. However, the quality understanding of their structure and function relationship is often hampered by the lack of efficient methods for the synthesis of sufficient amounts of pure structurally well-defined carbohydrate molecules. One of the long-standing challenging problems in synthetic carbohydrate chemistry is stereoselective construction of β-mannopyranosides. In this presentation, an approach for stereoselective synthesis of β-mannosides via cesium carbonate-mediated anomeric O-alkylation of partially protected D-mannose will be discussed. In addition, recent efforts from our group in mechanistic studies of this β-mannosylation as well as its application in the synthesis of complex carbohydrate molecules will be presented.

β-Mannosylation via cesium carbonate-mediated anomeric O-alkylation: Mechanistic studies and synthetic applications

256th National Meeting (2018)

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