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<p>In this study, we optimized a previously reported method for preparing bicyclic iminosugars from <i>D</i>-ribose tosylate. Through systematic screening and optimization of the reaction conditions, bicyclic iminosugars containing <i>O</i>-, <i>S</i>-, and <i>N</i>-glycosides were successfully prepared with yields of up to 99% and excellent stereoselectivity. Based on the formation of compound <b>I-2-1</b>, we hypothesize that the reaction proceeds <i>via</i> imine cation intermediates. Key improvenments over prior studies include the substitution of toluene with CH<sub>2</sub>Cl<sub>2</sub> as the solvent and the incorporation of Et<sub>3</sub>N as an acid-binding agent, both of which significantly enhanced the reaction yield and stereoselectivity. Furthermore, we successfully modified two of the products with a butyryl group, demonstrating the potential for further modification and subsequent biological activity studies.</p>

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Stereoselective Synthesis and Mechanism of Bicyclic Iminosugars

  • 期刊论文

  • 发表日期：

    2025年3月3日

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  • Tao Li,
  • Ying Zheng,
  • Lin Guo,
  • Yanping Xie,
  • Yiling Wang,
  • Ziyu Li,
  • Shicheng Hou,
  • Xiaoping Liu,
  • Chun Hu

摘要

In this study, we optimized a previously reported method for preparing bicyclic iminosugars from D-ribose tosylate. Through systematic screening and optimization of the reaction conditions, bicyclic iminosugars containing O-, S-, and N-glycosides were successfully prepared with yields of up to 99% and excellent stereoselectivity. Based on the formation of compound I-2-1, we hypothesize that the reaction proceeds via imine cation intermediates. Key improvenments over prior studies include the substitution of toluene with CH2Cl2 as the solvent and the incorporation of Et3N as an acid-binding agent, both of which significantly enhanced the reaction yield and stereoselectivity. Furthermore, we successfully modified two of the products with a butyryl group, demonstrating the potential for further modification and subsequent biological activity studies.