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<p><i>C</i>-Alkyl glycosides are found in natural products and are indispensable in drug development programs, owing to their diverse range of medicinal properties. Two-component reactions involving glycosyl radical addition are well documented and proved efficient for the <i>C</i>-alkyl glycosides synthesis. However, multicomponent reactions for the rapid and controllable construction of structurally diversified <i>C</i>-alkyl glycosides in a single step remains a significant challenge due to the issues associated with balancing reactivity, compatibility, and selectivity. Herein, we report an NHC and photoredox co-catalyzed three-component method to access complex and valuable <i>C</i>-alkyl glycosides. This protocol exhibits broad substrate scope and excellent chemo- and regioselectivity. Furthermore, nine types of sugars are compatible with this reaction. In addition, the generality of this catalytic strategy was further highlighted by the potential for scalable production, the feasibility of further modifications of the products and its successful application in the late-stage functionalization of pharmaceutical skeletons.</p>

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Modular assembly of complex C-alkyl glycoside enabled via cooperative NHC and photoredox catalysis

  • 期刊论文

  • 发表日期：

    2025年1月2日

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  • Rui-Qiang Jiao,
  • Ming Li,
  • Xi Chen,
  • Mei-Ze Xu,
  • Tian Ding,
  • Xiao-Ping Gong,
  • Zhuo-Mei Li,
  • Xue-Yuan Liu,
  • Yong-Min Liang

摘要

C-Alkyl glycosides are found in natural products and are indispensable in drug development programs, owing to their diverse range of medicinal properties. Two-component reactions involving glycosyl radical addition are well documented and proved efficient for the C-alkyl glycosides synthesis. However, multicomponent reactions for the rapid and controllable construction of structurally diversified C-alkyl glycosides in a single step remains a significant challenge due to the issues associated with balancing reactivity, compatibility, and selectivity. Herein, we report an NHC and photoredox co-catalyzed three-component method to access complex and valuable C-alkyl glycosides. This protocol exhibits broad substrate scope and excellent chemo- and regioselectivity. Furthermore, nine types of sugars are compatible with this reaction. In addition, the generality of this catalytic strategy was further highlighted by the potential for scalable production, the feasibility of further modifications of the products and its successful application in the late-stage functionalization of pharmaceutical skeletons.