The first polymer-assisted solution-phase synthesis of deoxyglycosides

Area of Science:

• Organic Chemistry
• Carbohydrate Chemistry
• Synthetic Chemistry

Background:

• Glycosylation is crucial for synthesizing complex carbohydrates.
• Developing efficient and versatile glycosylation protocols remains a challenge.
• 2-Deoxyglycosides are important structural motifs in various biologically active molecules.

Purpose of the Study:

• To develop a novel glycosylation protocol for the synthesis of 2-deoxyglycosides.
• To utilize polymer-bound reagents for improved efficiency and purification.
• To demonstrate the applicability of the method in synthesizing complex glycosylated natural products and analogs.

Main Methods:

• Transformation of glycals into 2-iodoglycosyl acetates using polymer-bound bis(acetoxy)iodate(I).
• Activation of the anomeric center with polymer-bound silyl triflate.
• Glycosylation of various glycosyl acceptors with the activated intermediates.

Main Results:

• The developed protocol efficiently synthesizes 2-deoxy-2-iodoglycosides in very good yields.
• The use of polymer-bound reagents simplifies purification and allows for reagent recovery.
• The method was successfully applied in multistep syntheses of glycosylated testosterone and a complex oligosaccharide.

Conclusions:

• A robust and efficient polymer-supported glycosylation protocol for 2-deoxyglycoside synthesis has been established.
• This method offers advantages in terms of yield, purification, and applicability to complex targets.
• The protocol provides a valuable tool for carbohydrate chemists and drug discovery efforts.