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Related Experiment Videos

Efficient sialylation with phenyltrifluoroacetimidates as leaving groups.

Sutang Cai1, Biao Yu

  • 1State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

Organic Letters
|October 11, 2003
PubMed
Summary

This study introduces an improved method for sialylation using N-phenyltrifluoroacetimidates and TMSOTf. This approach enhances the Schmidt glycosylation reaction, offering a more efficient way to synthesize sialylated compounds.

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis

Background:

  • Direct sialylation is crucial for synthesizing biologically active glycoconjugates.
  • Existing methods for sialylation often face limitations in scope and efficiency.

Purpose of the Study:

  • To develop a more effective protocol for direct sialylation.
  • To expand the applicability of the Schmidt glycosylation reaction.

Main Methods:

  • Utilizing N-phenyltrifluoroacetimidates as glycosyl donors.
  • Employing a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf) as a promoter.

Main Results:

  • The developed method demonstrates favorable comparison with previous direct sialylation protocols.
  • The scope of the Schmidt glycosylation reaction is significantly expanded.

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Conclusions:

  • The new sialylation strategy offers a robust and efficient alternative.
  • This advancement facilitates broader access to complex sialylated molecules.