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

Sweeney, J.B. and Bethel, P.A. and Gill, D.M. and Ochocińska, A.M. and Walsh, A.E.J. and Walton, S.M. (2019) Synthesis of a protected keto-lysidine analogue via improved preparation of arabino-isocytosine nucleosides. Organic Letters, 21 (7). pp. 2004-2007. ISSN 1523-7060

[img]
Text (Revised ol-2019-00086u)
Revised_ol_2019_00086u.pdf - Accepted Version
Available under License Creative Commons Attribution-NonCommercial.

Download (827kB)

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.

Item Type:
Journal Article
Journal or Publication Title:
Organic Letters
Additional Information:
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
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1600/1606
Subjects:
ID Code:
133191
Deposited By:
Deposited On:
22 Jun 2019 09:09
Refereed?:
Yes
Published?:
Published
Last Modified:
20 Sep 2020 05:30