Photoinitiated thiol-ene mediated functionalisation of 4,5-enoses

Area of Science:

• Carbohydrate Chemistry
• Organic Synthesis
• Photochemistry

Background:

• Thioglycosides are crucial in medicinal chemistry and chemical biology.
• Traditional synthesis methods can be lengthy and lack efficiency.
• Photoinitiated reactions offer novel synthetic pathways.

Purpose of the Study:

• To develop an efficient method for synthesizing C4-position, S-linked glycosides.
• To explore the application of photoinitiated thiol-ene reactions in saccharide chemistry.
• To enable fluorescent labeling of disaccharides.

Main Methods:

• Radical-mediated hydrothiolation of 4,5-unsaturated saccharides.
• Utilizing photoinitiation for the thiol-ene reaction.
• Investigating a diverse range of unsaturated saccharide substrates.

Main Results:

• High yields of S-linked glycosides were achieved.
• Complete regioselectivity and good diastereoselectivity were observed.
• 1,2-Ethanedithiol adducts provided a suitable thiol handle for further modification.

Conclusions:

• Photoinitiated thiol-ene reaction is a powerful tool for thioglycoside synthesis.
• The developed method offers efficient access to C4-functionalized glycosides.
• The resulting products are amenable to tagging and fluorescent labeling applications.