Mediated Electrochemical Oxidation of Nucleosides to Their 5'-Carboxylic Acid Derivatives.

ABSTRACT: Nucleoside 5'-carboxylic acids are important synthetic targets, but most existing methods to access these compounds use (super)stoichiometric chemical oxidants to oxidize the primary alcohol. The present study introduces an aminoxyl-mediated electrochemical method for oxidation of nucleosides and ribosugars to afford their 5'-carboxylic acid derivatives. The optimized conditions employ 4-acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl (ACT) as the aminoxyl mediator in a water/acetonitrile solvent mixture with tetraethylammonium bicarbonate or monohydrogen phosphate as a base within an undivided electrolysis cell. The reaction tolerates diverse functionality at the nucleobase and sugar positions and is showcased in the oxidation of 10 different substrates, including a 10 g scale oxidation of

SUBMITTER: Abrams DJ 

PROVIDER: S-EPMC12043033 | biostudies-literature | 2025 Apr

REPOSITORIES: biostudies-literature