Efficient access to 3′-deoxy-3′-(4-substituted-1,2,3-triazol-1-yl)-thymidine derivatives via ligand-promoted CuAAC - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Tetrahedron Année : 2021

Efficient access to 3′-deoxy-3′-(4-substituted-1,2,3-triazol-1-yl)-thymidine derivatives via ligand-promoted CuAAC

Résumé

Herein we describe an efficient and rapid access to 3 0-deoxy-3 0-(4-substituted-1,2,3-triazol-1-yl)thymidine derivatives using 1,3-dipolar cycloaddition reaction catalyzed by copper(I). Innovative conditions allow us to generate target compounds in a one-pot reaction mixing 3 0-azido-3 0-deoxythymidine, alkyne, copper sulfate pentahydrate, sodium ascorbate and tris(benzyltriazolylmethyl)amine in a water:tert-butanol solvent mixture. Rapid treatment of the reaction and subsequent flash purification chromatography afforded pure compounds in an overall yield of 71e100%. All eleven synthesized compounds were identified on the basis of their spectral data analysis (1 H, 13 C, 2D NMR and highresolution mass spectra).
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hal-03457261 , version 1 (09-05-2022)

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Laura Garlatti, Raphaël Huet, Karine Alvarez. Efficient access to 3′-deoxy-3′-(4-substituted-1,2,3-triazol-1-yl)-thymidine derivatives via ligand-promoted CuAAC. Tetrahedron, 2021, 92, pp.132252. ⟨10.1016/j.tet.2021.132252⟩. ⟨hal-03457261⟩
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