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Selective deoxygenation and modification at C2' of nucleosides
Nucleic Acids Symposium Series
|January 1, 1982
Summary
Nucleosides can be selectively protected using tetraisopropyldisiloxane (TPDS) for efficient 2' functionalization. This method provides high yields for synthesizing various deoxy-nucleoside analogues, including ribo and arabino forms.
Area of Science:
- Organic Chemistry
- Nucleoside Chemistry
- Synthetic Methodology
Background:
- Nucleoside modifications are crucial for developing therapeutic agents and biochemical tools.
- Selective protection of hydroxyl groups in nucleosides is a key challenge in synthetic chemistry.
- Existing methods often lack efficiency or stereoselectivity for specific modifications.
Purpose of the Study:
- To develop a high-yielding and selective method for protecting nucleosides.
- To enable efficient functionalization at the 2'-position of nucleosides.
- To provide stereoselective routes to 2'-deoxy-nucleoside analogues.
Main Methods:
- Treatment of nucleosides with 1,1,3,3-tetraisopropyl-1,3-dichlorodisiloxane (TPDS) in pyridine.
- Selective protection of 3' and 5' hydroxyl groups.
- Deoxygenation, oxidation-reduction, triflation, and nucleophilic displacement reactions.
Main Results:
- High yields of 3',5'-O-(1,1,3,3-tetraisopropyldisilox-1,3-diyl) nucleoside derivatives.
- Efficient functionalization at the 2'-position of protected nucleosides.
- Stereoselective synthesis of 2'-deoxy-beta-D-erythro-pentofuranosyl and 2'-deoxy-alpha-D-erythro-pentofuranosyl compounds.
- Access to beta-arabinonucleosides and 2'-deoxy-2'-substituted ribo and arabino analogues.
Conclusions:
- The TPDS protection strategy offers a versatile and efficient route for nucleoside modification.
- This methodology facilitates the synthesis of diverse deoxy-nucleoside analogues with controlled stereochemistry.
- The developed methods are valuable for exploring structure-activity relationships and creating novel nucleoside-based compounds.