Highly stereoselective synthesis of α-glycosylated carboxylic acids by phenanthroline catalysis.

ABSTRACT: Carbohydrate molecules with an α-glycosylated carboxylic acid motif provide access to biologically relevant chemical space but are difficult to synthesize with high selectivity. To address this challenge, we report a mild and operationally simple protocol to synthesize a wide range of functionally and structurally diverse α-glycosylated carboxylic acids in good yields with high diastereoselectivity. Although there is no apparent correlation between reaction conversion and pK _a of carboxylic acids, we found that carboxylic acids with a pK _a of 4-5 provide high selectivity while those of a pK _a of 2.5 or lower do not. Our strategy utilizes readily available 2,9-dibutyl-1,10-phenanthroline as an effective nucleophilic catalyst to displace

SUBMITTER: Alom NE 

PROVIDER: S-EPMC11347974 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature