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Development, Scope, and Catalyst Selection in Boron-Catalyzed Iterative Glycosylation.

Kishor R Harale1, Chandana Sunil1, Girish C Sati1

  • 1Department of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, Michigan 48109-1055, United States.

Journal of the American Chemical Society
|December 8, 2025
PubMed
Summary
This summary is machine-generated.

This study demonstrates boron-catalyzed iterative glycosylations for efficient synthesis of complex carbohydrates. The reaction sequence is controlled by silane structure, enabling selective formation of glycosidic bonds.

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Area of Science:

  • Organic Chemistry
  • Carbohydrate Chemistry
  • Synthetic Chemistry

Background:

  • Boron-catalyzed glycosylations offer a direct route to glycosidic bonds using glycosyl fluorides and silyl ethers.
  • Iterative glycosylation strategies are crucial for building complex oligosaccharides efficiently.

Purpose of the Study:

  • To investigate the application of boron-catalyzed glycosylations in iterative sequences.
  • To determine the factors controlling selectivity in iterative glycosylations with silyl ether acceptors.

Main Methods:

  • Utilized boron trifluoride etherate (BF3·OEt2) as a catalyst for glycosylation reactions.
  • Employed 19F NMR spectroscopy to monitor reaction rates and selectivities.
  • Investigated the influence of trialkyl silane structure on glycosylation outcomes.

Main Results:

  • Established that the trialkyl silane structure dictates the sequence of glycosidic bond formation, overriding precursor reactivity.
  • Identified BF3·OEt2 as a highly effective catalyst for iterative glycosylations.
  • Successfully synthesized tri- and tetrasaccharides from monosaccharide precursors via site- and stereoselective iterative glycosylations.

Conclusions:

  • Boron-catalyzed iterative glycosylation is a powerful method for constructing complex carbohydrates.
  • The developed protocol allows for precise control over glycosidic bond formation, enabling efficient synthesis of oligosaccharides.