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

被引：36

作者：

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
]}

机构：

[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

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 14期

基金：

巴西圣保罗研究基金会;

关键词：

D-Glucal; 1,2,3-Triazole; Cycloaddition; Click chemistry; Selenosugars; 1,3-DIPOLAR CYCLOADDITION REACTION; ULTRASOUND-ASSISTED SYNTHESIS; GLYCOGEN-PHOSPHORYLASE; SYMMETRICAL BIARYLS; ORGANOSELENIUM; INHIBITION; ALKYNES; DESIGN; ACID; DRUG;

D O I：

10.1016/j.tetlet.2012.01.102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：1742 / 1747

页数：6

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