| Synthesis of 3'-substituted-2',3'-deoxy-2'-methylidenepyrimidine nucleosides. | |
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MedLine Citation:
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PMID: 1289836 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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2'-deoxy-2'-methylideneuridine derivative 9 was converted into 2',3'-didehydro-2',3'-dideoxy-2'-phenyl-selenomethyl derivative 16, which was treated with NCS and tert-butyl carbamate to afford 3'-amino derivative 18 via a [2,3]-sigmatropic rearrangement. Treatment of 9 with DAST gave a mixture of 2',3'-didehydro-2', 3'-dideoxy-2'-fluoromethyl derivative 19 and 3'-"up"-fluoro-2'-methylidene derivative 20 in a ratio of 1.5 : 1. On the other hand, when 12 was treated with DAST, 19 and 3'-"down"-fluoro-2'-methylidene derivative 21 were obtained in a ratio of 1 : 1.6. These nucleosides were converted into the corresponding cytidine derivatives 4, 6, and 8, respectively. The reaction mechanisms as well as biological activity of these compounds will also be discussed. |
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Authors:
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A A Hassan; A Matsuda |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Nucleic acids symposium series Volume: - ISSN: 0261-3166 ISO Abbreviation: Nucleic Acids Symp. Ser. Publication Date: 1992 |
Date Detail:
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Created Date: 1993-03-25 Completed Date: 1993-03-25 Revised Date: 2000-12-18 |
Medline Journal Info:
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Nlm Unique ID: 8007206 Medline TA: Nucleic Acids Symp Ser Country: ENGLAND |
Other Details:
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Languages: eng Pagination: 85-6 Citation Subset: IM |
Affiliation:
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Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Deoxycytidine
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analogs & derivatives,
chemistry Pyrimidine Nucleosides / chemical synthesis* |
| Chemical | |
Reg. No./Substance:
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0/Pyrimidine Nucleosides; 119804-96-5/2'-methyl-2'-deoxyidenecytidine; 951-77-9/Deoxycytidine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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