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Glycosyl fluorides in glycosidations
1Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan. toshima@applc.keio.ac.jp
Carbohydrate Research
|September 1, 2000
Summary
Recent advancements in chemical glycosylation utilize glycosyl fluorides as versatile donors. These methods efficiently produce O-glycosides and C-glycosyl compounds using various activating reagents.
Area of Science:
- Carbohydrate Chemistry
- Organic Synthesis
- Glycosylation Methods
Background:
- Glycosyl fluorides are increasingly recognized as valuable glycosyl donors.
- Efficient synthesis of O- and C-glycosides is crucial in medicinal chemistry and materials science.
Purpose of the Study:
- To review recent progress in chemical O-glycosidation and C-glycosylation using glycosyl fluorides.
- To highlight the diverse range of activating reagents and reaction conditions employed.
Main Methods:
- Activation of pyranosyl and furanosyl fluorides using a variety of Lewis acids and fluorophilic reagents.
- Reaction of activated glycosyl fluorides with alcohols for O-glycosidation.
- Reaction of activated glycosyl fluorides with nucleophiles for C-glycosylation.
Main Results:
- High yields of O-glycosides were achieved using numerous activating systems.
- Various C-glycosyl derivatives, including aryl, allyl, and alkyl types, were successfully synthesized.
- Glycosyl fluorides demonstrated broad applicability in both O- and C-glycosylation.
Conclusions:
- Glycosyl fluorides are effective and versatile glycosyl donors for both O- and C-glycosylation.
- A wide array of activating reagents enables efficient synthesis of diverse glycosylated compounds.
- These methods offer promising routes for accessing complex carbohydrate structures.