Synlett
DOI: 10.1055/s-0036-1590968
letter
© Georg Thieme Verlag Stuttgart · New York

Scalable Synthesis of 2,2′-Anhydro-arabinofuranosyl Imidazoles

Shaun Stairs, Matthew W. Powner*
  • Department of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ, UK   Email: matthew.powner@ucl.ac.uk
This work was supported by the Simons Foundation (318881) and the Engineering and Physical Sciences Research Council (EP/K004980/1)
Further Information

Publication History

Received: 09 June 2017

Accepted after revision: 28 June 2017

Publication Date:
27 July 2017 (eFirst)

Abstract

We report the efficient and scalable synthesis of 2,2′-anhydro-5-amino-1-β-arabinofuranosylimidazole-4-carboxamide and 2,2′-anhydro-5-amino-1-β-arabinofuranosylimidazole-4-carbonitrile from commercial arabino-adenosine. 2,2′-Anhydro-5-amino-1-β-arabinofuranosylimidazole-4-carboxamide is synthesised in only five steps with a single chromatographic purification. Additionally, we report a high-yielding, three-step conversion of 2,2′-anhydro-5-amino-1-β-arabinofuranosylimidazole-4-carboxamide into 2,2′-anhydro-5-amino-1-β-arabinofuranosylimidazole-4-carbonitrile. They are proposed key intermediates of the divergent prebiotic synthesis of ribonucleotides and this facile synthesis is anticipated to be instrumental in continued investigation of the origins of nucleotides.

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