2023
DOI: 10.1055/a-2174-2554
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Serendipitous Synthesis of 5-Hydroxyuridine from 2′,3′-O-Isopropylidene N4-Acetylcytidine by Hypervalent Iodine(III)-Mediated Reaction

Carine Baraguey,
Françoise Debart,
Michael Smietana
et al.

Abstract: Whereas BAIB-TEMPO oxidation of 2’,3’-O-TBDMS-N4-acetylcytidine results in the expected 5'-carboxylic acid nucleoside, its 2',3'-O-isopropylidene analogue reacts in a radically different way. We have demonstrated here that hypervalent iodine(III) in water triggers an unprecedented oxidative cyclization leading to a mixture of C5-substituted O6,5'-cyclo-5,6-dihydro-uridines. This mixture of cyclouridines can be opened under basic conditions and, after deprotection, yields 5-hydroxyuridine, an important post-tra… Show more

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