Synthesis of 3'-deoxy-4'-thionucleosides

Area of Science:

• Medicinal Chemistry
• Organic Synthesis
• Drug Discovery

Background:

• 3 -deoxy-4 -thionucleosides are investigated for antiviral and antitumor properties.
• Developing efficient synthetic routes is crucial for drug candidate exploration.

Purpose of the Study:

• To achieve the racemic synthesis of 3 -deoxy-4 -thionucleosides.
• To establish a method applicable for enantioselective synthesis.

Main Methods:

• A key step involved a tandem intra- and intermolecular S_N2 reaction of a thioepoxide to build the 3 -deoxy-4 -thioribose skeleton.
• Pummerer reaction followed by Vorbrüggen-type glycosylation was employed.
• The synthesis can be adapted for enantioselective routes using chiral oxiranes.

Main Results:

• Successful racemic synthesis of 3 -deoxy-4 -thionucleosides was accomplished.
• The synthetic strategy is versatile and allows for enantioselective approaches.

Conclusions:

• The developed method provides a viable route to 3 -deoxy-4 -thionucleosides.
• This synthesis opens avenues for further investigation of these compounds as therapeutic agents.