Efficient access to 3′-deoxy-3′-(4-substituted-1,2,3-triazol-1-yl)-thymidine derivatives via ligand-promoted CuAAC
2021
Garlatti, Laura | Huet, Raphaël | Alvarez, Karine
Herein we describe an efficient and rapid access to 3′-deoxy-3′-(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′-azido-3′-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 71–100%. All eleven synthesized compounds were identified on the basis of their spectral data analysis (¹H, ¹³C, 2D NMR and high-resolution mass spectra).
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