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Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors
Jeroen D C Codée1, Leendert J van den Bos, Remy E J N Litjens
1Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Organic Letters
|May 24, 2003
Summary
A new sequential glycosylation method efficiently creates complex carbohydrates like the alpha-Gal epitope and hyaluronan trisaccharides. This one-pot procedure uses 1-hydroxyl and thiodonors for synthesizing thiodisaccharides and trisaccharides.
Area of Science:
- Carbohydrate Chemistry
- Organic Synthesis
- Glycoscience
Background:
- Glycosylation is crucial for synthesizing complex carbohydrates, essential in biological processes.
- Developing efficient and selective glycosylation methods remains a key challenge in carbohydrate chemistry.
- Sequential glycosylation strategies are needed for building oligosaccharides with defined linkages.
Purpose of the Study:
- To develop a novel sequential glycosylation procedure.
- To combine 1-hydroxyl and thiodonors in a single synthetic strategy.
- To efficiently assemble biologically relevant carbohydrate epitopes.
Main Methods:
- Utilized a Ph(2)SO/Tf(2)O-mediated dehydrative condensation.
- Employed a sequential approach involving 1-hydroxyl donors and thioglycosides.
- Developed a one-pot procedure for synthesizing thiodisaccharides and trisaccharides.
Main Results:
- Achieved good yields of thiodisaccharides from 1-hydroxyl donors and thioglycosides.
- Successfully synthesized trisaccharides by activating thiodisaccharides with the same system.
- Efficiently assembled the alpha-Gal epitope and a hyaluronan trisaccharide in one pot.
Conclusions:
- The novel sequential glycosylation procedure is effective for synthesizing complex carbohydrates.
- The one-pot strategy offers an efficient route to valuable oligosaccharide structures.
- This method provides a powerful tool for carbohydrate synthesis and glycobiology research.