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초록· 키워드
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Conformationally locked nucleosides are important in searching selective agonists and antagonists for P2Y receptors. There were two previous synthetic works of the crucial intermediate, cyclopentenyl alcohol (3), which had some inefficiency like using too strong dianionic base and synthesis of racemate. Here we describes a facile synthesis of the intermediate using Sharpless epoxidation and the opening of epoxide ring using zinc, followed by Grubb's metathesis as key steps. The intermediate was converted to the southern bicyclo[3.2.0]heptane for confirming its usefulness.
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참고문헌 (15)
참고문헌 신청
Obika, S / 2002 / Synthesis and conformation of 3',4'-BNA monomers, 3'-O,4'-C Methyleneribonucleosides / Tetrahedron 58:3039
Obika, S / 2001 / 2'-O,4'-C-Methylene bridged nucleic acid (2',4'-BNA): synthesis and triplex-forming properties / Bioorg. Med. Chem 9:1001
Kauppinen, S / 2005 / Locked nucleic acid (LNA): High affinity targeting of RNA for diagnostics and therapeutics / Drug Discovery Today 10:287
Kim, H. S / 2003 / Synthesis of a novel conformationally locked carbcyclic nucleoside ring system / Org. Lett 5:1665
Kim, S. A / 2007 / Synthesis of conformationally locked methanocarba-uridine as a precursor for nucleotides agonizing P2Y6 receptor / Synlett 7:1055
Obika, S / 2001 / 2'-O,4'-C-Methylene bridged nucleic acid (2',4'-BNA): synthesis and triplex-forming properties / Bioorg. Med. Chem 9:1001
Kauppinen, S / 2005 / Locked nucleic acid (LNA): High affinity targeting of RNA for diagnostics and therapeutics / Drug Discovery Today 10:287
Kim, H. S / 2003 / Synthesis of a novel conformationally locked carbcyclic nucleoside ring system / Org. Lett 5:1665
Kim, S. A / 2007 / Synthesis of conformationally locked methanocarba-uridine as a precursor for nucleotides agonizing P2Y6 receptor / Synlett 7:1055
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