Copper(I)-Catalyzed Tandem One-Pot Synthesis of Bis(1,2,3-Triazoles) and Tetrakis (1,2,3-Triazole) Glycoconjugates

Abstract

The work describes the copper (I)-catalyzed convenient synthesis of 5,5′-bis-1,2,3-triazoles by reacting glycosyl azides with terminal alkynes in the presence of di-tert-butyl peroxide (DTBP) as oxidant in refluxing toluene. The reaction proceeds through intramolecular ‘click’ followed by Csp2.Csp2 bond formation in the successive steps under one-pot conditions. The devised protocol is further extended to access biocompatible tetrakis(1,2,3-triazolyl) sialoconjugates under a two-step pathway followed by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. The developed glycoconjugates have been characterized using extensive spectroscopic analysis, including NMR (1H & 13C), IR, and high-resolution mass spectrometry data, and also a single-crystal X-ray of compound 5e. Notably, the reaction proceeds in a one-pot fashion with a high atom economy, where a wide substrate scope with diversity in products finally validates the importance of the devised protocol. © 2025 Wiley-VCH GmbH.