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  • Revised ol-2019-00086u

    Rights statement: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.orglett.9b00086

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    Embargo ends: 12/03/20

    Available under license: CC BY-NC: Creative Commons Attribution-NonCommercial 4.0 International License

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Synthesis of a protected keto-lysidine analogue via improved preparation of arabino-isocytosine nucleosides

Research output: Contribution to journalLetter

Published
  • J.B. Sweeney
  • P.A. Bethel
  • D.M. Gill
  • A.M. Ochocińska
  • A.E.J. Walsh
  • S.M. Walton
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<mark>Journal publication date</mark>5/04/2019
<mark>Journal</mark>Organic Letters
Issue number7
Volume21
Number of pages4
Pages (from-to)2004-2007
Publication statusPublished
Early online date12/03/19
Original languageEnglish

Abstract

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 (t)RNA.

Bibliographic note

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.orglett.9b00086