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

Anwar Shamim; Stanley N. S. Vasconcelos; Isadora Maria de Oliveira; Joel S. Reis; Daniel C. Pimenta; Julio Zukerman-Schpector; Hélio A. Stefani

doi:10.1055/s-0036-1589090

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(23): 5183-5196
DOI: 10.1055/s-0036-1589090

paper

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

Anwar Shamim

^aInstituto de Química, Av. Prof. Lineu Prestes, 748,05508-000, Universidade de São Paulo, São Paulo – SP, Brasil

,

Stanley N. S. Vasconcelos

^bFaculdade de Ciências Farmacêuticas, Av. Prof. Lineu Prestes, 580, 05508-00, Universidade de São Paulo, São Paulo – SP, Brasil eMail: hstefani@usp.br

,

Isadora Maria de Oliveira

^aInstituto de Química, Av. Prof. Lineu Prestes, 748,05508-000, Universidade de São Paulo, São Paulo – SP, Brasil

,

Joel S. Reis

^bFaculdade de Ciências Farmacêuticas, Av. Prof. Lineu Prestes, 580, 05508-00, Universidade de São Paulo, São Paulo – SP, Brasil eMail: hstefani@usp.br

,

Daniel C. Pimenta

^cInstituto Butantã, São Paulo – SP, Brasil

,

Julio Zukerman-Schpector

^dDepartamento de Química, Universidade Federal de São Carlos, São Carlos –SP, Brasil

,

Hélio A. Stefani*

^bFaculdade de Ciências Farmacêuticas, Av. Prof. Lineu Prestes, 580, 05508-00, Universidade de São Paulo, São Paulo – SP, Brasil eMail: hstefani@usp.br

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Abstract

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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.

Key words

d-glucal - azide - click chemistry - bis(triazole) - tris(triazole)

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