4.5 Article

Direct Anodic N-α Hydroxylation: Accessing Versatile Intermediates for Azanucleoside Derivatives

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 11, Issue 4, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100756

Keywords

anodic oxidation; azanucleoside; electrochemistry; hydroxylation; iminium ion

Funding

  1. JSPS KAKENHI [17K19222, 19H00930, 19K22272, 20H03072, 20J11925]
  2. JST CREST [JPMJCR19R2]
  3. Grants-in-Aid for Scientific Research [19K22272, 19H00930, 20J11925, 20H03072] Funding Source: KAKEN

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Ring oxygen-substituted artificial nucleosides, with furanose structure, exhibit unique pharmacological activities as anticancer and antiviral agents, even when not incorporated into oligonucleotides. Direct anodic N-alpha hydroxylation in aqueous media is demonstrated as a practical synthetic method for versatile intermediates in the preparation of azanucleoside derivatives.
Furanose ring oxygen-substituted artificial nucleosides show unique pharmacological activities even without incorporation into oligonucleotides, and are used as anticancer and antiviral agents. Practical synthetic routes to such nucleosides are of exceptional importance to enhance the development of (oligo)nucleotide therapeutics. Herein, we demonstrate that direct anodic N-alpha hydroxylation is possible in aqueous media to realize the practical synthesis of these versatile intermediates for azanucleoside derivatives.

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