Hydroxamate-directed access to β-Kdo glycosides.

Area of Science:

• Carbohydrate Chemistry
• Organic Synthesis
• Glycosylation

Background:

• Transient aziridinone and azaoxyallyl cations are key intermediates in organic synthesis.
• Hydroxamates offer unique reactivity compared to traditional amides in certain reactions.

Purpose of the Study:

• To extend the reaction repertoire of α-halohydroxamates for glycosyl donor design.
• To achieve stereoselective synthesis of β-Kdo glycosides.
• To elucidate the role of the hydroxamate moiety in glycosylation reactions.

Main Methods:

• Designing novel Kdo-glycosyl donors by installing a hydroxamate moiety at the anomeric center.
• Utilizing the reactivity of α-halohydroxamates for generating reactive intermediates.
• Performing control experiments to compare hydroxamate and amide functionalities.

Main Results:

• The newly designed Kdo-glycosyl donors proved highly effective for glycosylation.
• Stereoselective access to β-Kdo glycosides was achieved.
• Control experiments highlighted the crucial role of the hydroxamate group over the amide group.

Conclusions:

• The installation of a hydroxamate moiety at the anomeric center of Kdo derivatives is a viable strategy for creating effective glycosyl donors.
• This method provides a stereoselective route to β-Kdo glycosides.
• Hydroxamates are superior to amides in this specific glycosylation context.