Synthesis 2017; 49(23): 5183-5196
DOI: 10.1055/s-0036-1589090
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Glycosyl Azides and Their Applications Using CuAAC Click Chemistry to Generate Bis- and Tris(triazolyl)glycosyl Derivatives

Anwar Shamima, Stanley N. S. Vasconcelosb, Isadora Maria de Oliveiraa, Joel S. Reisb, Daniel C. Pimentac, Julio Zukerman-Schpectord, Hélio A. Stefani*b
  • aInstituto de Química, Av. Prof. Lineu Prestes, 748,05508-000, Universidade de São Paulo, São Paulo – SP, Brasil
  • bFaculdade de Ciências Farmacêuticas, Av. Prof. Lineu Prestes, 580, 05508-00, Universidade de São Paulo, São Paulo – SP, Brasil   Email: hstefani@usp.br
  • cInstituto Butantã, São Paulo – SP, Brasil
  • dDepartamento de Química, Universidade Federal de São Carlos, São Carlos –SP, Brasil
The authors are grateful for the financial support provided by FAPESP - São Paulo Research Foundation (FAPESP) (Grant 2012/00424-2), CAPES (to A.S.) and CNPq – the National Council for Scientific and Technological Development (306119/2014-5 to H.A.S.).
Further Information

Publication History

Received: 24 May 2017

Accepted after revision: 11 July 2017

Publication Date:
10 August 2017 (eFirst)

Abstract

2,3-Unsaturated C-(triazolyl)glycosyl acetates have been synthesized from 3,4,6-tri-O-acetyl-d-glucal using C-glycosylation and click chemistry and were then used in a palladium-catalyzed Tsuji–Trost type allylic azidation reaction to afford the corresponding regioisomeric glucal-azide derivatives. Copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions with these glucal-based allylic azides using CuI as the catalyst, led to the corresponding glucal-based bis(triazole) derivatives. Performing further functional group modification and another click (CuAAC) reaction with each of these bis(triazolyl) glycosyl derivatives afforded tris(triazolyl)glycosyl derivatives. Two libraries of regioisomeric bis(triazole) derivatives and a small library of regioisomeric tris(triazole) derivatives of glucal were then synthesized using different alkynes.

Supporting Information

 
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