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Synthesis of C-glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri-\(\varvec{O}\)-acetyl-D-glucal

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Abstract

We have developed an efficient, CuI-catalyzed, microwave-assisted method for the synthesis of bis-1,2,3-triazole derivatives starting from a 3,4,6-tri-\(O\)-acetyl-d-glucal-derived mesylate. This mesylate was obtained from 3,4,6-tri-\(O\)-acetyl-d-glucal through \(C\)-glycosidation, deprotection of acetate groups to alcohols, and selective mesylation of the primary alcohol. This mesylate moiety was then converted to an azide through a microwave-assisted method with good yield. The azide, once synthesized, was then treated with different terminal alkynes in the presence of CuI to synthesize various bis-triazoles in high yields and short reaction times.

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Acknowledgments

The authors gratefully acknowledge financial support from the São Paulo Research Foundation (FAPESP, Grant 2012/00424-2 and fellowship to FBS 2013/20553-4) and National Council for Scientific and Technological Development (CNPq) for a fellowship (308.320/2010–7 to HAS).

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Authors and Affiliations

  1. Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil

    Anwar Shamim

  2. Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil

    Frederico B. Souza, Gustavo H. G. Trossini, Fernando M. Gatti & Hélio A. Stefani

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  1. Anwar Shamim
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Correspondence to Hélio A. Stefani.

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Shamim, A., Souza, F.B., Trossini, G.H.G. et al. Synthesis of C-glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri-\(\varvec{O}\)-acetyl-D-glucal. Mol Divers 19, 423–434 (2015). https://doi.org/10.1007/s11030-014-9564-0

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