Supported Synthesis of Adenosine Nucleotides and Derivatives on a Benzene‐Centered Tripodal Soluble Support - Archive ouverte HAL Accéder directement au contenu
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.
Fichier principal
Vignette du fichier
ejoc.202100544.pdf (3.53 Mo) Télécharger le fichier
Origine Fichiers éditeurs autorisés sur une archive ouverte

Dates et versions

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

Identifiants

Citer

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⟩
18 Consultations
16 Téléchargements

Altmetric

Partager

Gmail Mastodon Facebook X LinkedIn More