Sequential Regiodivergent Polyol Sulfonylation and Functionalization Enable Precise Engineering of Carbohydrates.

ABSTRACT: Substituent functionalization of unprotected and partially protected carbohydrates with controlled regioselectivity remains challenging due to the difficulty in differentiating hydroxyl groups with similar reactivities. This study presents an efficient protocol for site-specific modification through a "two-stage," regiodivergent polyol tagging and functionalization strategy. To achieve effective tagging, we developed two complementary Ag₂CO₃-ligand-based regimes that enable the regioselective sulfonylation of cis-diol and trans-diol in carbohydrates, controlled by simply toggling the presence of a [Pd] catalyst. Competition experiments and DFT simulations elucidated the underlying dual mechanisms accounting for the regioselectivity. [Pd] catalyst complex

SUBMITTER: Zhou S 

PROVIDER: S-EPMC12848703 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature