Photochemical Iron-Catalyzed Decarboxylative S-Glycosylation
Yun Liu1, Jianing Yu1, Yun-Kun Su1
1Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education & Hubei Key Laboratory of Catalysis and Materials Science, School of Chemistry and Materials Science, South-Central Minzu University, Wuhan 430074, China.
Organic Letters
|April 9, 2026
Summary
Researchers developed a new method for synthesizing alkyl thioglycosides, crucial in drug design. This iron-catalyzed reaction offers a direct route, overcoming previous challenges and enabling diverse applications in medicinal chemistry.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Carbohydrate Chemistry
Background:
- Alkyl thioglycosides are vital structural units in pharmaceuticals, acting as carbohydrate mimics.
- Their synthesis often faces challenges, particularly with controlling stereochemistry at the anomeric center.
Purpose of the Study:
- To establish a novel and efficient protocol for the direct synthesis of alkyl thioglycosides.
- To overcome the limitations of existing methods, especially concerning anomeric control.
Main Methods:
- Photoinduced iron-catalyzed decarboxylative coupling reaction.
- Utilized glycosyl thiosulfonates and primary, secondary, and tertiary alkyl carboxylic acids.
Main Results:
- Successfully synthesized a diverse array of alkyl thioglycosides.
- Achieved complete stereoretention at the anomeric center, a significant advancement.
- Demonstrated applicability in late-stage glycodiversification of complex molecules.
Conclusions:
- The developed protocol provides a direct and stereoselective method for alkyl thioglycoside synthesis.
- This strategy offers a valuable tool for drug design and the preparation of bioactive compounds.
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