Site-Selective Distal Arylation of Sugars Enabled by Cyclic Acetals
Shuai Zhang1,2, Julia Ordóñez1,2, Christian O Blanco1
1Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain.
This study introduces a new nickel-catalyzed method using cyclic acetals to create complex glycosides. This approach provides selective access to valuable sugar derivatives for drug development.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Catalysis
Background:
- Glycosides are crucial in medicinal chemistry.
- Synthesizing glycosides with carbon-carbon linkages can be challenging.
- Current methods often lack site selectivity for complex structures.
Purpose of the Study:
- To develop a novel photoinduced nickel-catalyzed method for synthesizing glycosides.
- To utilize cyclic acetals as versatile precursors for C-C bond formation.
- To access elusive glycosides with specific structural features.
Main Methods:
- Photoinduced nickel catalysis.
- Employing cyclic acetals as starting materials.
- Selective C-C bond formation at positions distal to the anomeric center.
Main Results:
- Successful synthesis of glycosides with C-C linkages.
- High site selectivity achieved in the reaction.
- Demonstrated utility of cyclic acetals in this transformation.
Conclusions:
- This protocol offers a new synthetic route to valuable glycoside compounds.
- The method provides access to previously elusive structures.
- Potential applications in developing novel sugar-based therapeutics with lipophilic chains.
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