A broadly applicable stereospecific glycosylation

Area of Science:

• Carbohydrate Chemistry
• Organic Synthesis
• Glycobiology

Background:

• Developing a general strategy for stereospecific glycosidic linkage construction is crucial for complex glycan synthesis.
• Stereospecific glycosylations via S_N2 mechanisms are ideal but lack generality across diverse sugar types.

Purpose of the Study:

• To present a novel stereospecific glycosylation method with broad applicability.
• To overcome limitations in current glycosylation strategies for complex carbohydrate synthesis.

Main Methods:

• Employing mild activation with an electrophilic bromine reagent for glycosylation.
• Testing the method across a wide range of monosaccharides, including hexopyranoses and pentofuranoses.

Main Results:

• Achieved complete inversion of anomeric configuration and excellent yields in numerous glycosylations.
• Demonstrated reliability in multistep oligosaccharide syntheses and automated glycan assembly.

Conclusions:

• The developed method provides a general and stereospecific approach to glycosylation.
• This breakthrough facilitates complex glycan synthesis and advances automated glycan assembly.