Synthesis of 1,2,3-triazolylpyranosides through click chemistry reaction |
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| Authors: | Hélio A. Stefani Nathália C.S. Silva Flávia Manarin Diogo S. Lüdtke Julio Zukerman-Schpector Lucas Sousa Madureira Edward R.T. Tiekink |
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| Affiliation: | 1. Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, CEP 05508-000, Brazil;2. Instituto de Química, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS, Brazil;3. Departamento de Química, Universidade Federal de São Carlos, São Carlos, SP, Brazil;4. Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia |
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| Abstract: | We have developed an efficient method for the synthesis of functionalized C-glycosyl 1,2,3-triazoles through a Cu(I)-promoted azide–alkyne 1,3-dipolar cycloaddition between a TMS-protected C-alkynyl-glycoside and organic azides. The reaction was accelerated by ultrasound irradiation and the addition of a base was not necessary to obtain the 1,2,3-triazole product. Moreover, further manipulation of the products led to chiral molecules with a C-glycoside linkage. |
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