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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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Nucleosides with 1,4-dioxane as sugar moiety.

Andreas Stahl Madsen¹, Niels Langkjaer, Jesper Wengel

¹Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, Campusvej 55, 5230 Odense M, Denmark. asm@ifk.sdu.dk

Nucleic Acids Symposium Series (2004)

|September 9, 2008

Summary

This summary is machine-generated.

A new method synthesizes novel nucleosides using a 1,4-dioxane sugar. This approach introduces a second anomeric center, enabling the creation of unique phosphoramidites for further chemical applications.

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Area of Science:

Organic Chemistry
Nucleoside Analogue Synthesis
Medicinal Chemistry

Background:

Nucleoside analogues are crucial in antiviral and anticancer therapies.
Exploring novel sugar moieties can lead to compounds with improved pharmacological profiles.
1,4-Dioxane derivatives offer unique structural features not commonly found in natural nucleosides.

Purpose of the Study:

To develop a novel synthetic route for nucleosides incorporating a 1,4-dioxane ring as the sugar moiety.
To functionalize the 1,4-dioxane moiety at a second anomeric center.
To prepare diastereomeric phosphoramidites from these novel nucleosides.

Main Methods:

Development of a synthetic pathway to construct 1,4-dioxane-based nucleosides.
Phosphitylation reaction at the newly introduced anomeric center of the dioxane ring.
Characterization of the resulting diastereomeric phosphoramidites.

Main Results:

Successful synthesis of novel nucleosides featuring a 1,4-dioxane sugar scaffold.
Demonstration of phosphitylation at the second anomeric center of the dioxane moiety.
Obtained a diastereomeric mixture of the corresponding phosphoramidites.

Conclusions:

A viable synthetic route to novel 1,4-dioxane nucleosides has been established.
The developed method allows for the preparation of unique phosphoramidite building blocks.
These novel phosphoramidites hold potential for the synthesis of modified oligonucleotides and drug discovery.