Stereoselective Synthesis of 2-Deoxythiosugars from Glycals
Xueying You1, Yifei Cai1, Chenyu Xiao1
1Hubei Key Laboratory of Natural Products Research and Development, Key Laboratory of Functional Yeast (China National Light Industry), College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China.
Molecules (Basel, Switzerland)
|November 26, 2022
Summary
Researchers developed a new method for synthesizing stable 2-deoxythioglycosides. This efficient process uses silver triflate catalysis for high stereoselectivity, yielding valuable compounds for drug discovery.
Area of Science:
- Carbohydrate Chemistry
- Organic Synthesis
- Medicinal Chemistry
Background:
- 2-deoxythiosugars offer enhanced stability compared to 2-deoxysugars.
- 2-deoxysugar motifs are prevalent in bioactive natural products and pharmaceuticals.
Purpose of the Study:
- To develop an effective and direct method for stereoselective synthesis of alpha-2-deoxythioglycosides.
- To explore the scope of the developed methodology using various thiols and thiophenols.
Main Methods:
- Utilized silver triflate (AgOTf) as a catalyst for the glycosylation reaction.
- Investigated the reaction with a range of alkyl thiols and thiophenols.
- Applied the method to synthesize S-linked disaccharides and perform late-stage glycosylation.
Main Results:
- Achieved excellent alpha-selectivity in the synthesis of 2-deoxythioglycosides.
- Obtained desired products in good yields across various substrates.
- Successfully synthesized S-linked disaccharides and functionalized bioactive molecules.
Conclusions:
- The developed AgOTf-catalyzed method provides efficient and stereoselective access to alpha-2-deoxythioglycosides.
- This methodology is versatile, applicable to complex structures like disaccharides and late-stage functionalization of natural products and drug candidates.
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