A streamlined strategy for aglycone assembly and glycosylation

Area of Science:

• Organic Chemistry
• Carbohydrate Chemistry
• Synthetic Chemistry

Background:

• Traditional synthesis of complex carbohydrates and aglycones often involves multiple steps and distinct reagents.
• Developing versatile reagents that can perform multiple functions simplifies synthetic routes.

Purpose of the Study:

• To introduce carbohydrate-derived silane reagents with dual reactivity.
• To demonstrate their utility in nickel-catalyzed reductive coupling and glycosylation reactions.
• To enable efficient construction of carbon-carbon frameworks and stereochemical control in complex molecule synthesis.

Main Methods:

• Utilizing carbohydrate-derived silane reagents as reductants in nickel-catalyzed aldehyde-alkyne reductive coupling.
• Employing the same silane reagents as glycosyl donors for subsequent intramolecular glycosylation.
• Investigating the simultaneous assembly of the aglycone framework and glycosylation site.

Main Results:

• Successful application of carbohydrate-derived silanes as multipurpose reagents.
• Efficient formation of carbon-carbon bonds via reductive coupling.
• Stereoselective installation of glycosidic linkages through intramolecular glycosylation.
• Streamlined synthesis of molecules with defined aglycone structures and glycosylation patterns.

Conclusions:

• Carbohydrate-derived silanes offer a powerful and versatile strategy for complex molecule synthesis.
• This dual-function approach simplifies synthetic pathways, reducing step count and improving efficiency.
• The methodology provides a platform for constructing intricate carbon skeletons and controlling stereochemistry in glycosylation.