β-Mannopyranoside is one of the key glycosidic linkages existing in numerous biologically significant targets, such as N-linked glycans, bacterial capsular polysaccharides, fungal metabolites, glycolipids, and etc. Stereoselective construction of β-mannopyranosides, however, remains as a long-standing challenge due to the steric effect of the axial C2- substituents as well as the absence of anomeric effect and anchimeric assistance, albeit remarkable success has been achieved. Recently, we developed a direct and efficient method for the synthesis of β-mannopyranosides via Cs2CO3-mediated anomeric O-alkylation of mannose-derived lactols with suitable electrophiles. In this presentation, we will describe our mechanistic studies of this umpolung-type β-mannosylation through extensive chemical experiments and computational studies. In addition, application of this β-mannosylation to the syntheses of select complex carbohydrate targets will also be discussed.

Mechanistic investigations of β-mannosylation via Cs2CO3-mediated anomeric O-alkylation and synthesis of complex biologically significant carbohydrate molecules

2019 Fall National Meeting

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