Synthesis of 1,2,3-triazolylpyranosides through click chemistry reaction

Author(s)

Stefani, Helio A. ^[1] ; Silva, Nathalia C. S. ^[1] ; Manarin, Flavia ^[1] ; Luedtke, Diogo S. ^[2] ; Zukerman-Schpector, Julio ^[3] ; Madureira, Lucas Sousa ^[3] ; Tiekink, Edward R. T. ^[4]

Affiliation

^[1] Univ Sao Paulo, Dept Farm, Fac Ciencias Farmaceut, BR-05508000 Sao Paulo - Brazil

^[2] Univ Fed Rio Grande do Sul, Inst Quim, Porto Alegre, RS - Brazil

^[3] Univ Fed Sao Carlos, Dept Quim, BR-13560 Sao Carlos, SP - Brazil

^[4] Univ Malaya, Dept Chem, Kuala Lumpur 50603 - Malaysia

• Document type: Journal article
• Source: Tetrahedron Letters; v. 53, n. 14, p. 1742-1747, APR 4 2012.
• Web of Science Citations: 30

Abstract

We have developed an efficient method for the synthesis of functionalized C-glycosyl 1,2,3-triazoles through a Cu(1)-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. (C) 2012 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 10/15677-8 - Synthesis of alpha-substituted styrenes
• Grantee: Flávia Giovana Manarin
• Support Opportunities: Scholarships in Brazil - Post-Doctoral