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Preparation of thianucleoside derivatives
J Uenishi1, M Motoyama, K Takahashi
1Department of Chemistry, Okayama University of Science, Japan.
Nucleic Acids Symposium Series
|January 1, 1992
Summary
The synthesis of 1'-deoxy-4'-thioribonucleoside was achieved in eight steps. A key coupling reaction preferentially yielded the desired beta-isomer using specific mediators.
Area of Science:
- Organic Chemistry
- Nucleoside Chemistry
- Medicinal Chemistry
Background:
- Nucleoside analogs are crucial in antiviral and anticancer therapies.
- Thionucleosides, with sulfur replacing oxygen, offer unique biological properties.
- Efficient synthesis of modified nucleosides is essential for drug development.
Purpose of the Study:
- To synthesize a novel 1 ahydrogen-4 ahydrogen-thioribonucleoside.
- To establish an efficient synthetic route for this thionucleoside analog.
- To investigate stereoselective glycosylation methods for thionucleoside synthesis.
Main Methods:
- Multi-step synthesis starting from an acyclic allylic alcohol.
- Key glycosylation step involving the coupling of a thiafuranose moiety with a pyrimidine base.
- Optimization of reaction conditions using Lewis acids like TMSOTf and SnCl4.
Main Results:
- Successful synthesis of 1 ahydrogen-4 ahydrogen-thioribonucleoside (1) in eight steps.
- Identification of TMSOTf and SnCl4 as effective mediators for the coupling reaction.
- Preferential formation of the beta-anomer during the glycosylation step.
Conclusions:
- An 8-step synthetic route to 1 ahydrogen-4 ahydrogen-thioribonucleoside was developed.
- The use of TMSOTf and SnCl4 facilitates stereoselective synthesis of the beta-isomer.
- This methodology provides a valuable approach for accessing thionucleoside analogs.