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Site-Selective C─H Bond Functionalization of Sugars.

Elena Stepanova1, Andrey Shatskiy2, Ivan Doroshenko1

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Angewandte Chemie (International Ed. in English)
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PubMed
Summary

This study introduces a new method for creating complex C-functionalized sugars. The novel traceless tethering approach enables site-selective and stereocontrolled synthesis of these important biologically-active compounds.

Keywords:
C-H Bond ActivationCarbohydratesPhotoredox CatalysisRadicalsVisible light

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Medicinal Chemistry

Background:

  • Non-typical C-functionalized sugars are biologically important but difficult to synthesize.
  • Current methods often require extensive protecting groups or lack selectivity.

Purpose of the Study:

  • To develop a facile, site-selective, and stereocontrolled method for C-functionalizing sugars.
  • To overcome limitations of existing synthetic strategies for accessing novel carbohydrate derivatives.

Main Methods:

  • Utilized a silyl-based redox-active tethering group for direct attachment to unprotected sugars.
  • Employed a photochemically-promoted 1,6-hydrogen atom transfer (HAT) mechanism for C-functionalization.
  • The tethering group transforms into a removable silyl protecting group post-reaction.

Main Results:

  • Achieved facile, site-selective, and stereocontrolled C-functionalization of various unprotected carbohydrates.
  • Demonstrated compatibility with sensitive aglycons and diverse coupling partners.
  • Developed a straightforward and scalable route to C-functionalized carbohydrate conjugates.

Conclusions:

  • The traceless tethering approach offers a significant advancement in synthesizing non-typical C-functionalized sugars.
  • This method provides efficient access to pharmaceutically relevant carbohydrate structures.
  • The protocol is versatile and scalable for broader synthetic applications.