Molecular Diversity

, Volume 19, Issue 3, pp 423–434 | Cite as

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

  • Anwar Shamim
  • Frederico B. Souza
  • Gustavo H. G. Trossini
  • Fernando M. Gatti
  • Hélio A. Stefani
Full-Length Paper


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.


Microwave d-Glucal Click chemistry \(1{, }2{, }\)3-Triazole Flourescence Ultrasound 



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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Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  • Anwar Shamim
    • 1
  • Frederico B. Souza
    • 2
  • Gustavo H. G. Trossini
    • 2
  • Fernando M. Gatti
    • 2
  • Hélio A. Stefani
    • 2
  1. 1.Instituto de QuímicaUniversidade de São PauloSão PauloBrazil
  2. 2.Departamento de Farmácia, Faculdade de Ciências FarmacêuticasUniversidade de São PauloSão PauloBrazil

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