Stereoselective Synthesis and Mechanism of Bicyclic Iminosugars

doi:10.1007/s40242-025-4225-7

Chemical Research in Chinese Universities ›› 2025, Vol. 41 ›› Issue (3): 539-544.doi: 10.1007/s40242-025-4225-7

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Stereoselective Synthesis and Mechanism of Bicyclic Iminosugars

LI Tao, ZHENG Ying, GUO Lin, XIE Yanping, WANG Yiling, LI Ziyu, HOU Shicheng, LIU Xiaoping, HU Chun

School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China

Received:2024-11-18 Revised:2025-01-14 Online:2025-06-01 Published:2025-05-27
Contact: HOU Shicheng,E-mail:shichenghou@syphu.edu.cn;LIU Xiaoping,E-mail:xiaopingliu@syphu.edu.cn;HU Chun,E-mail:chunhu@syphu.edu.cn E-mail:shichenghou@syphu.edu.cn;xiaopingliu@syphu.edu.cn;chunhu@syphu.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (No. 21342006), the Health and Medical Research Fund of Hong Kong, China (No. 18170352), and the Program for Innovative Research Team of the Ministry of Education of China (No. IRT_14R36).

Abstract

Abstract: 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.

Key words: Iminosugar, Reaction mechanism, Imine cation

LI Tao, ZHENG Ying, GUO Lin, XIE Yanping, WANG Yiling, LI Ziyu, HOU Shicheng, LIU Xiaoping, HU Chun. Stereoselective Synthesis and Mechanism of Bicyclic Iminosugars[J]. Chemical Research in Chinese Universities, 2025, 41(3): 539-544.

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Stereoselective Synthesis and Mechanism of Bicyclic Iminosugars

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