Versatile gold catalyzed transglycosidation at ambient temperature.

Area of Science:

• Organic Chemistry
• Carbohydrate Chemistry
• Catalysis

Background:

• Glycosidation reactions are crucial in synthesizing complex carbohydrates and glycoconjugates.
• Developing stable glycosyl donors that react efficiently under mild conditions is an ongoing challenge.
• Gold catalysis offers a promising avenue for promoting glycosidation due to its unique reactivity.

Purpose of the Study:

• To identify novel, stable alkyl glycosyl donors for gold-catalyzed glycosidation.
• To investigate the mechanism of glycosidation using these new donors at room temperature.
• To demonstrate the utility of 1-ethynylcyclohexanyl glycosides in glycosylation reactions.

Main Methods:

• Synthesis of 1-ethynylcyclohexanyl glycosides.
• Gold-catalyzed glycosidation reactions using these novel donors.
• Mechanistic studies involving spectroscopic analysis and computational methods.

Main Results:

• 1-ethynylcyclohexanyl glycosides were successfully synthesized and characterized.
• These novel donors efficiently participate in glycosidation reactions catalyzed by gold salts at room temperature.
• Mechanistic investigations revealed that the leaving group extrudes simply, indicating a straightforward reaction pathway.

Conclusions:

• 1-ethynylcyclohexanyl glycosides represent a new class of stable and effective glycosyl donors.
• Gold-catalyzed glycosidation using these donors provides a mild and efficient method for glycosidic bond formation.
• The facile extrusion of the leaving group simplifies the reaction mechanism and enhances synthetic applicability.