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Using Molecular Iodine in Direct Oxidative Condensation of Aldoses with Diamines: An Improved Synthesis of Aldo-benzimidazoles and Aldo-naphthimidazoles for Carbohydrate Analysis.

  作者 Lin, Chunchi;Lai, Po-Ting;Liao, Sylvain Kuo-Shiang;Hung, Wei-Ting;Yang, Wen-Bin;Fang, Jim-Min;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2008年73-10;  页码  3848-3853  
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[摘要]A practical method has been developed for conversion of unprotected and unmodified aldoses to aldo-benzimidazoles, e.g. I, and aldo-naphthimidazoles. Using iodine as an oxidant or promoter in acetic acid soln., a series of mono-, di-, and trialdoses, including those contg. carboxyl and acetamido groups, undergo an oxidative condensation reaction with o-phenylenediamine or 2,3-naphthalenediamine at room temp. to give the aldo-benzimidazole and aldo-naphthimidazole products in high yields. No cleavage of the glycosidic bond occurs under such mild reaction conditions. The compn. anal. of saccharides is realized by the HPLC anal. of the fluorescent naphthimidazole derivs.

 
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