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Regioselective O-arylation of 6-hydroxy Groups in Carbohydrates

Overview
Journal Carbohydr Res
Publisher Elsevier
Date 2025 Mar 6
PMID 40048879
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Abstract

We report an efficient method for regioselective O-arylation of the 6-hydroxy group of carbohydrates. The reaction involves a nucleophilic aromatic substitution reaction (SAr) using electron-deficient arenes under mild conditions. Regioselectively monoarylated carbohydrate derivative was produced smoothly in the reaction by fine-tuning with the base. The pentafluoropyridine (P1) in combination with N, N-diisopropylethylamine (DIPEA) was successfully converted to regioselective O-arylated products of different positional hydroxy group free sugar derivatives with various functional groups.