Synthesis 2025; 57(07): 1319-1328
DOI: 10.1055/s-0043-1773520
paper

Exploring the Reactivity of α-Halo Ethers with 2,3′-Anhydrothymidine and 2,2′-Anhydrouridine Derivatives

Vincent Baran
,
Quentin Foucart
,
Arnaud Tessier
,
Jacques Lebreton
,
Monique Mathé-Allainmat

This research was funded by the French Ministère de l’Enseignement Supérieur et de la Recherche, the Centre National de la Recherche Scientifique­ (Chimie-CNRS) for the national GAVO project and by the Région Bretagne-Pays de Loire. V.B. thanks the CNRS and Région Bretagne-Pays de Loire for Ph.D. funding.


Abstract

An efficient and simple procedure for direct halogenation of nucleoside furanose rings is developed using commercial α-halo ether reagents. The methodology enables simultaneous protection of the N 3-pyrimidine and halogenation of the ribose ring, starting from the corresponding readily accessible anhydro nucleosides. Several 2′- or 3′-halo-nucleoside derivatives are prepared in good yields under very mild reaction conditions.

Supporting Information



Publikationsverlauf

Eingereicht: 25. Oktober 2024

Angenommen nach Revision: 12. Januar 2025

Artikel online veröffentlicht:
04. März 2025

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