| Autor: |
Marianne R. Spada, Robyn S. Klein, Brian A. Otter, Mallela S. P. Sarma, Sreenivasulu Megati |
| Rok vydání: |
1997 |
| Předmět: |
|
| Zdroj: |
Nucleosides and Nucleotides. 16:1983-1998 |
| ISSN: |
0732-8311 |
| DOI: |
10.1080/07328319708002549 |
| Popis: |
Two approaches to the synthesis of the title compounds are described. In the first route, a reactive 5-oxo-6-methylene pyrimidine intermediate that is generated by treating the bis-acetylated or bis-benzoylated nucleosides 10 and 11 with sodium hydroxide undergoes intramolecular attack by the 5′-thiol group to afford the 5-hydroxy cyclonucleoside 12. In the second and higher yielding approach, the S5′,6-methano linkage is established by an internal allylic displacement reaction that occurs when the 5-bromo-6-methyl nucleoside 24 is treated with base. The conformational properties of S5′,6-methano-5′-thiouridine (3) and certain long-range spin-spin couplings observed in the NMR spectra of the intermediate nucleosides are discussed. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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