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User-Friendly Thioglycoside Preactivation via Instant Sulfenyl Chloride Generation.

Xingchun Sun1, Xiao-Lin Zhang2, Xin-Ru Qiao1

  • 1Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.

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This study introduces a stable, user-friendly method for generating sulfenyl chloride activators for one-pot oligosaccharide synthesis. This approach simplifies complex carbohydrate assembly, enabling efficient access to biologically relevant structures.

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Glycobiology

Background:

  • Thioglycoside preactivation is crucial for one-pot oligosaccharide assembly.
  • Existing methods rely on unstable sulfenyl chloride activators, limiting practical application.

Purpose of the Study:

  • To develop a user-friendly and stable method for generating sulfenyl chloride activators.
  • To enable efficient and rapid one-pot oligosaccharide synthesis using a novel manifold.

Main Methods:

  • A manifold was designed to generate sulfenyl chlorides in seconds from common thiols and N-chlorosuccinimide.
  • Succinimide precipitates, leaving a clear supernatant as a drop-in activator solution.
  • The protocol was tested for substrate scope, including stereoselective glycosylation and iterative sequences.

Main Results:

  • The developed manifold provides a stable and readily usable sulfenyl chloride activator solution.
  • The protocol demonstrates broad substrate scope and compatibility with complex synthetic strategies.
  • A human milk tetrasaccharide was synthesized concisely, showcasing rapid one-pot access to biologically relevant motifs.

Conclusions:

  • This user-friendly manifold offers a significant advancement in thioglycoside chemistry.
  • The method facilitates efficient and rapid assembly of complex oligosaccharides, including biologically relevant structures.
  • This approach simplifies the synthesis of valuable carbohydrate targets.