Glycosyl Sulfonates Beyond Triflates

Area of Science:

• Carbohydrate Chemistry
• Organic Synthesis
• Glycosylation Reactions

Background:

• Glycosyl triflates are common glycosylation intermediates, but other glycosyl sulfonates are less explored.
• Sulfonate reactivity varies widely, offering potential for novel stereoselective reactions.
• Developing selective glycosylation methods is crucial for synthesizing complex carbohydrates.

Purpose of the Study:

• To investigate the potential of glycosyl sulfonates in stereoselective glycosylation.
• To develop novel methods for β-specific glycosylation reactions.
• To explore the use of 2-deoxy-sugar tosylates as glycosyl donors.

Main Methods:

• Utilizing various glycosyl sulfonates as donors in glycosylation reactions.
• Investigating the stereochemical outcomes of these reactions.
• Synthesizing 2-deoxy-sugar tosylates and evaluating their efficacy.
• Optimizing reaction conditions to achieve high selectivity.

Main Results:

• 2-deoxy-sugar tosylates were identified as highly selective donors for β-glycoside synthesis.
• This approach has been successfully applied to construct deoxy-sugar oligosaccharides and natural products.
• Matching sulfonate reactivity to the sugar donor enabled highly selective S_N2-glycosylations across various substrates.

Conclusions:

• Glycosyl sulfonates represent an underutilized class of reagents for glycosylation.
• The developed methods provide efficient access to β-glycosides, particularly deoxy-sugars.
• Tailoring sulfonate reactivity is key to achieving high stereoselectivity in glycosylation.