Regioselective synthesis of 5-trifluoromethyl-1,2,3-triazole nucleoside analogues via TBS-directed 1,3-dipolar cycloaddition reaction

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• 作者：Zhiru Xiong^a ; Xiao-Long Qiu^b ; Yangen Huang^a ; Feng-Ling Qing^a ; ^b ; ^{flq@mail.sioc.ac.cn}
• 关键词：Nucleoside analogues ; Triazole ; Trifluoromethyl group ; 1 ; 3-Dipolar cycloaddition ; Regioselective synthesis
• 刊名：Journal of Fluorine Chemistry
• 出版年：2011
• 出版时间：March 2011
• 年：2011
• 卷：132
• 期：3
• 页码：166-174
• 全文大小：1159 K

文摘

Herein described was a straightforward method for the highly regioselective synthesis of 5-trifluoromethyl-1,2,3-triazole nucleoside analogues, which featured the utilization of tert-butyldimethylsilyl (TBDMS) group as the directing group in the 1,3-dipolar cycloaddition reactions. 4-tert-Butyldimethylsilyl-5-trifluoromethyl-1,2,3-triazole nucleoside analogues were generated as the only cycloaddition products in moderate yields (15–79 % ) via the treatment of glycosyl azides with 3,3,3-trifluoro-1-tert-butyldimethylsilylpropyne 1 in toluene at 85 °C. Removal of TBS groups in these triazole cycloadducts with tetrabutylammonium fluoride (TBAF) smoothly afforded the various 5-trifluoromethyl-1,5-disubstituted 1,2,3-triazole nucleoside analogues in good yields (40–88 % ).