Self-Promoted Stereoselective Glycosylations - Past, Present, Future
Natasha Videcrantz Faurschou1, Christian Marcus Pedersen1
1Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100, Copenhagen O, Denmark.
Chemical Record (New York, N.Y.)
|May 24, 2021
Summary
Self-promoted glycosylations offer easy and stereoselective carbohydrate synthesis. This review details their mechanisms and highlights their potential for developing novel glycosylation methods.
Area of Science:
- Carbohydrate Chemistry
- Organic Synthesis
Background:
- Self-promoted glycosylations are underutilized despite advantages.
- These reactions offer high stereoselectivity and ease of execution.
- Glycosylation is crucial for synthesizing complex carbohydrates.
Purpose of the Study:
- To review the field of self-promoted glycosylations.
- To discuss the mechanistic aspects and stereoselectivity of these reactions.
- To highlight the potential of self-promoted glycosylation strategies.
Main Methods:
- Literature review of self-promoted glycosylation reactions.
- Analysis of mechanistic pathways and stereochemical outcomes.
- Discussion of various glycosyl donors, including trichloroacetimidates.
Main Results:
- Self-promoted glycosylations are often highly stereoselective.
- Trichloroacetimidate donors are commonly employed.
- Alternative donors have also been successfully used.
Conclusions:
- Self-promoted glycosylation strategies are valuable tools in carbohydrate synthesis.
- Further research can lead to new stereoselective glycosylation methodologies.
- These methods offer a promising avenue for efficient synthesis of complex glycans.
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