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Efficient Copper‐Catalyzed Highly Stereoselective Synthesis of Unprotected C‐Acyl Manno‐, Rhamno‐ and Lyxopyranosides

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Due to their high stability towards enzymatic hydrolysis C -acyl glycosidic compounds are useful synthetic intermediates for potential candidates in drug discovery. Syntheses for C -acyl mannosides have remained scarce and usually employ donors obtained from lengthy syntheses. Furthermore, syntheses of unprotected C- acyl mannosides have not been reported so far, due to the incapability of the C -acyl mannoside motif with deprotection conditions for protective groups commonly used in carbohydrate chemistry. Herein, we report an efficient and highly α‑selective four-step one-pot method for the synthesis of C -acyl α- d -manno-, l -rhamno- and d -lyxopyranosides from easily accessible persilylated monosaccharides and dithianes requiring only trace amounts of a copper source as catalyst and explain the crucial role of the catalyst by mechanistic studies. Furthermore, the C -acyl α-glycosides were easily isomerized to give rapid access to their β-anomers.

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