Expeditious Synthesis of 2-Deoxy-2-perfluoroalkyl Glycosides

Area of Science:

• Carbohydrate Chemistry
• Medicinal Chemistry
• Organic Synthesis

Background:

• Fluorine incorporation enhances drug properties.
• Synthesizing C2-perfluoroalkylated sugars is challenging.

Purpose of the Study:

• Develop an efficient synthesis for 2-deoxy-2-perfluoroalkyl glycosides.
• Expand the scope of fluorinated carbohydrate synthesis.
• Explore applications in drug discovery.

Main Methods:

• Utilized readily available glycals as starting materials.
• Employed gold(I)-catalyzed glycosylation reactions.
• Investigated photocatalytic generation of radicals for Giese additions and cross-couplings.

Main Results:

• Achieved efficient synthesis of diverse C-, N-, and O-glycosides (over 50 examples).
• Successfully synthesized novel 2-deoxy-2-CF3-substituted nucleoside analogues.
• Demonstrated Giese-type additions and cross-coupling reactions yielding potential antidiabetic drug candidates.

Conclusions:

• The developed protocol is efficient, cost-effective, and broadly applicable.
• 2-deoxy-2-CF3-modified glycosides show promising pharmacological properties.
• This synthetic platform facilitates the development of advanced carbohydrate-based therapeutics.