One-Step Aqueous Synthesis of Glycosyl Pyridinium Salts, Electrochemical Study, and Assessment of Utility as Precursors of Glycosyl Radicals Using Photoredox Catalysis.

ABSTRACT: A single step method for the production of unprotected glycosyl pyridinium salts has been developed involving treatment of the unprotected sugar with a pyridine, triethylamine, and either 2-chloro-1,3-dimethylimidazolinium chloride (DMC) or 2-chloro-1,3-dimethyl-1 H-benzimidazol-3-ium chloride (CDMBI) as an activator, in aqueous solution. Reaction efficiency is sensitive to steric effects, and in particular, ortho-substitution of the pyridine ring significantly decreased conversion to product; para-substitution of the pyridine ring is well tolerated. Cyclic voltammetry reveals that glycosyl pyridinium salts possess reduction potentials in the range of -0.9 to -1.4 V versus the standard calomel electrode, which are modulated by the electron effects of ring substituents. However, glycosyl py

SUBMITTER: Chong D 

PROVIDER: S-EPMC12518051 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature