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

Abstract : 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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https://hal.archives-ouvertes.fr/hal-03457261
Contributor : Karine ALVAREZ Connect in order to contact the contributor
Submitted on : Monday, May 9, 2022 - 9:40:22 AM
Last modification on : Tuesday, May 10, 2022 - 3:50:58 AM

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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, Elsevier, 2021, 92, pp.132252. ⟨10.1016/j.tet.2021.132252⟩. ⟨hal-03457261⟩

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