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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

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Sonication-assisted oligomannoside synthesis.

Christabel T Tanifum¹, Cheng-Wei T Chang

¹Department of Chemistry and Biochemistry, Utah State University, 0300 Old Main Hill, Logan, Utah 84322-0300, USA.

The Journal of Organic Chemistry

|December 10, 2008

Summary

This summary is machine-generated.

We developed a sonication-mediated glycosylation method for synthesizing biologically important oligomannosides. This efficient protocol activates even poorly reactive glycosyl donors, simplifying complex carbohydrate synthesis.

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Area of Science:

Carbohydrate Chemistry
Organic Synthesis
Sonochemistry

Background:

Oligomannosides are complex carbohydrates with significant biological roles.
Traditional glycosylation methods often struggle with activating less reactive glycosyl donors.
Efficient synthesis of specific oligomannosides is crucial for biological studies.

Purpose of the Study:

To develop a novel sonication-mediated protocol for oligomannoside synthesis.
To demonstrate the protocol's applicability to traditional glycosylation techniques.
To enable efficient synthesis of biologically relevant oligomannosides using challenging donors.

Main Methods:

Investigated the application of sonication in glycosylation reactions.
Developed a sonication-mediated protocol compatible with existing glycosylation methods.
Utilized sonication to activate low-reactivity glycosyl donors.

Main Results:

A convenient and efficient sonication-mediated glycosylation protocol was established.
The protocol successfully facilitated the synthesis of oligomannosides.
Low-reactivity glycosyl donors were effectively activated, enabling synthesis with high efficiency.

Conclusions:

Sonication provides an effective strategy for enhancing glycosylation reactions.
The developed protocol offers a versatile approach for synthesizing complex oligomannosides.
This method simplifies the preparation of biologically significant oligosaccharides.