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Article Dans Une Revue European Journal of Organic Chemistry Année : 2021

Supported Synthesis of Adenosine Nucleotides and Derivatives on a Benzene‐Centered Tripodal Soluble Support

Lucie Appy
  • Fonction : Auteur
Béatrice Roy

Résumé

The first soluble-phase synthesis of adenosine nucleotides including α,β and β,γ-methylene bisphosphonate analogues on a multi-pod support is reported. Anchoring of a 2',3'-protected purine nucleoside to the tripodal support via the nucleobase was successfully achieved using a microwave assisted Cu(I)catalyzed azide-alkyne cycloaddition. Then, phosphorylation was performed, followed by cleavage with aqueous ammonia to provide adenine derivatives, and finally deprotection. When using benzylamine instead of ammonia, a derivative with N 6benzylamine adenine as nucleobase was obtained. This methodology allows to access adenosine 5'-mono, di and triphosphates, as well as various analogues of pharmacological interest in modest to good yields.
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Dates et versions

hal-03811235 , version 1 (11-10-2022)

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Lucie Appy, Suzanne Peyrottes, Béatrice Roy. Supported Synthesis of Adenosine Nucleotides and Derivatives on a Benzene‐Centered Tripodal Soluble Support. European Journal of Organic Chemistry, 2021, 2022 (21), ⟨10.1002/ejoc.202100544⟩. ⟨hal-03811235⟩
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