Stereoselective Synthesis and Mechanism of Bicyclic Iminosugars

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.

Keywords

Iminosugar / Reaction mechanism / Imine cation

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Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH