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

TETRAHEDRON LETTERS

卷:53

Article

Stefani, Helio A.¹  Silva, Nathalia C. S.¹  Manarin, Flavia¹  Luedtke, Diogo S.²  Zukerman-Schpector, Julio³  Madureira, Lucas Sousa³  Tiekink, Edward R. T.⁴ 

[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

关键词: D-Glucal;    1,2,3-Triazole;    Cycloaddition;    Click chemistry;    Selenosugars;   

DOI  :  10.1016/j.tetlet.2012.01.102

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

Free