Synthesis of a Protected keto-Lysidine Analogue via Improved Preparation of Arabino-isoCytosine Nucleosides.

Org Lett

Department of Chemical Sciences, School of Applied Sciences , University of Huddersfield, Queensgate, Huddersfield , West Yorkshire HD1 3DH , U.K.

Published: April 2019

Anhydrouridines react with aliphatic amines to give N-alkyl isocytosines, but reported procedures often demand very long reaction times and can be low yielding, with narrow scope. A modified procedure for such reactions has been developed, using microwave irradiation, significantly reducing reaction time and allowing facile access to a diverse range of novel nucleosides on the gram scale. The method has been used to prepare a precursor to a novel analogue of lysidine, a naturally occurring iminonucleoside found in RNA.

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http://dx.doi.org/10.1021/acs.orglett.9b00086DOI Listing

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