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Aromatic O-glycosylation.

Mårten Jacobsson1, Jesper Malmberg, Ulf Ellervik

  • 1Organic Chemistry, Lund University, PO Box 124, SE-221 00 Lund, Sweden.

Carbohydrate Research
|May 3, 2006
PubMed
Summary

Synthesizing aromatic O-glycosylation involves choosing the right carbohydrate donor. This review provides practical guidelines for glycosylating electron-rich and electron-deficient aromatic compounds effectively.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Carbohydrate Chemistry

Background:

  • Aromatic O-glycosylation is crucial for synthesizing important natural products.
  • Phenols are challenging glycosylation substrates due to the electron-withdrawing nature of aromatic rings.

Purpose of the Study:

  • To review common and less common carbohydrate donors for aromatic O-glycosylation.
  • To provide practical examples and guidelines for glycosylating aromatic residues.

Main Methods:

  • Review of literature on aromatic O-glycosylation reactions.
  • Analysis of different carbohydrate donors: anomeric acetates, halides, trichloroacetimidates, and thioglycosides.
  • Categorization of glycosylation strategies based on aromatic aglycon properties.

Main Results:

  • Anomeric acetates and trichloroacetimidates are effective for electron-rich aromatics under acidic conditions.
  • Glycosyl halides are preferred for electron-deficient aromatics under basic conditions.
  • Guidelines are established for selecting appropriate donors and conditions.

Conclusions:

  • Effective aromatic O-glycosylation strategies depend on the electronic properties of the aromatic aglycon.
  • Selection of the correct carbohydrate donor and activation method is key to successful synthesis.
  • This review offers valuable insights for chemists targeting aromatic O-glycosides.

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