Iodosylbenzene-Promoted Glycosylation with Selenoglycosides: Application in One-Pot Glycosylation
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View abstract on PubMed
Summary
This summary is machine-generated.A new glycosylation method using selenoglycosides offers mild, efficient synthesis of complex carbohydrates. This technique enables orthogonal synthesis strategies, proving valuable for creating intricate oligosaccharides.
Area Of Science
- Carbohydrate Chemistry
- Organic Synthesis
- Glycosylation Methods
Background
- Efficient synthesis of complex glycosides is crucial for drug discovery and glycobiology.
- Developing orthogonal glycosylation strategies is key for constructing complex oligosaccharides.
- Selenoglycosides offer potential as versatile glycosyl donors.
Purpose Of The Study
- To develop a novel and efficient glycosylation method utilizing selenoglycosides.
- To demonstrate the orthogonality of selenoglycosides with thioglycosides.
- To showcase the utility of this method in synthesizing complex oligosaccharides.
Main Methods
- Glycosylation of selenoglycosides activated by iodosylbenzene.
- Evaluation of reaction conditions for mildness, speed, and efficiency.
- Assessment of protecting group tolerance and substrate scope.
- Demonstration of orthogonal synthesis with thioglycosides.
- Application in one-pot synthesis of β-(1→6) oligoglucans.
Main Results
- A novel, mild, fast, and efficient glycosylation method for selenoglycosides was established.
- The method exhibits high tolerance to diverse protecting groups and a broad substrate scope.
- Selenoglycosides demonstrated orthogonality to thioglycosides under iodosylbenzene promotion.
- High yields were achieved for the challenging glucuronidation reaction using acetyl-protected selenoglycoside.
- Successful one-pot synthesis of β-(1→6) oligoglucans confirmed the method's utility.
Conclusions
- The developed selenoglycoside-based glycosylation method is highly efficient and versatile.
- This method provides a valuable tool for synthesizing complex glycosides and oligosaccharides.
- The demonstrated orthogonality expands synthetic possibilities in carbohydrate chemistry.
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