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Synthesis of (±)-4′-ethynyl-5′,5′-difluoro-2′,3′-dehydro-3′-deoxy- carbocyclic thymidine: a difluoromethylidene analogue of promising anti-HIV agent Ed4T
Synthesis of (±)-4′-ethynyl-5′,5′-difluoro-2′,3′-dehydro-3′-deoxy-carbocyclic-thymidine ( 8) was carried out. The difluoromethylylidene group of 8 was constructed by the electrophilic fluorination to the cyclopentenone 11 by using Selectfluor ®. Introduction of thymine base was investigated based on...
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| Published in: | Tetrahedron 2009-09, Vol.65 (36), p.7630-7636 |
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| Main Authors: | , , , , , , , , |
| Format: | Article |
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| cited_by | cdi_FETCH-LOGICAL-c358t-e687888d5333de39b0bd932e224831f378d36818f2b549b7b9f454c7b4b699813 |
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| cites | cdi_FETCH-LOGICAL-c358t-e687888d5333de39b0bd932e224831f378d36818f2b549b7b9f454c7b4b699813 |
| container_end_page | 7636 |
| container_issue | 36 |
| container_start_page | 7630 |
| container_title | Tetrahedron |
| container_volume | 65 |
| creator | Kumamoto, Hiroki Haraguchi, Kazuhiro Ida, Mayumi Nakamura, Kazuo T. Kitagawa, Yasuyuki Hamasaki, Takayuki Baba, Masanori Matsubayashi, Satoko Shimbara Tanaka, Hiromichi |
| description | Synthesis of (±)-4′-ethynyl-5′,5′-difluoro-2′,3′-dehydro-3′-deoxy-carbocyclic-thymidine (
8) was carried out. The difluoromethylylidene group of
8 was constructed by the electrophilic fluorination to the cyclopentenone
11 by using Selectfluor
®. Introduction of thymine base was investigated based on the Mitsunobu reaction by employing cyclopentenyl allyl alcohols variously substituted at the 4-position. It was found the 4-methoxycarbonyl derivative
14 gave the highest selectivity both in terms of regio- and stereochemistry.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2009.06.095 |
| format | article |
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8) was carried out. The difluoromethylylidene group of
8 was constructed by the electrophilic fluorination to the cyclopentenone
11 by using Selectfluor
®. Introduction of thymine base was investigated based on the Mitsunobu reaction by employing cyclopentenyl allyl alcohols variously substituted at the 4-position. It was found the 4-methoxycarbonyl derivative
14 gave the highest selectivity both in terms of regio- and stereochemistry.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2009.06.095</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Biological and medical sciences ; Carbocyclic nucleoside ; Carbohydrates. Nucleosides and nucleotides ; Chemistry ; d4T ; Exact sciences and technology ; gem-Difluoromethylidene ; Human immunodeficiency virus ; Medical sciences ; Mitsunobu reaction ; Nucleosides, nucleotides and oligonucleotides ; Organic chemistry ; Pharmacology. Drug treatments ; Preparations and properties</subject><ispartof>Tetrahedron, 2009-09, Vol.65 (36), p.7630-7636</ispartof><rights>2009 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c358t-e687888d5333de39b0bd932e224831f378d36818f2b549b7b9f454c7b4b699813</citedby><cites>FETCH-LOGICAL-c358t-e687888d5333de39b0bd932e224831f378d36818f2b549b7b9f454c7b4b699813</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21825608$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Kumamoto, Hiroki</creatorcontrib><creatorcontrib>Haraguchi, Kazuhiro</creatorcontrib><creatorcontrib>Ida, Mayumi</creatorcontrib><creatorcontrib>Nakamura, Kazuo T.</creatorcontrib><creatorcontrib>Kitagawa, Yasuyuki</creatorcontrib><creatorcontrib>Hamasaki, Takayuki</creatorcontrib><creatorcontrib>Baba, Masanori</creatorcontrib><creatorcontrib>Matsubayashi, Satoko Shimbara</creatorcontrib><creatorcontrib>Tanaka, Hiromichi</creatorcontrib><title>Synthesis of (±)-4′-ethynyl-5′,5′-difluoro-2′,3′-dehydro-3′-deoxy- carbocyclic thymidine: a difluoromethylidene analogue of promising anti-HIV agent Ed4T</title><title>Tetrahedron</title><description>Synthesis of (±)-4′-ethynyl-5′,5′-difluoro-2′,3′-dehydro-3′-deoxy-carbocyclic-thymidine (
8) was carried out. The difluoromethylylidene group of
8 was constructed by the electrophilic fluorination to the cyclopentenone
11 by using Selectfluor
®. Introduction of thymine base was investigated based on the Mitsunobu reaction by employing cyclopentenyl allyl alcohols variously substituted at the 4-position. It was found the 4-methoxycarbonyl derivative
14 gave the highest selectivity both in terms of regio- and stereochemistry.
[Display omitted]</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Biological and medical sciences</subject><subject>Carbocyclic nucleoside</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>d4T</subject><subject>Exact sciences and technology</subject><subject>gem-Difluoromethylidene</subject><subject>Human immunodeficiency virus</subject><subject>Medical sciences</subject><subject>Mitsunobu reaction</subject><subject>Nucleosides, nucleotides and oligonucleotides</subject><subject>Organic chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Preparations and properties</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNp9UcuO1DAQjBBIDAsfwM0XEEg4tB9JHPaEVgu70kocWLhajt2Z8ShjL3EGkdt-zd7hE_gUvgSHGThy6VaXq6rbqqJ4yqBkwOrX23LCqeQAbQl1CW11r1gxWUtaSVbfL1YAEqgEDg-LRyltAYAxLlbF3cc5TBtMPpHYkxc_v7-k8tftD4rTZg7zQKs8vFoKdb4f9nGMlC-Q-APhZnYZOQ7x20yJNWMX7WwHb0n22HnnA74hhvzV7xbrwTsMSEwwQ1zvcdl9k5988mGd0cnTi8vPxKwxTOTcyevHxYPeDAmfHPtJ8end-fXZBb368P7y7O0VtaJSE8VaNUopVwkhHIq2g861giPnUgnWi0Y5USumet5Vsu2aru1lJW3Tya5uW8XESfH84Juv-bLHNOl8k8VhMAHjPmkODYgGIBPZgWjHmNKIvb4Z_c6Ms2agl0T0VudE9JKIhlrnRLLm2dHcJGuGfjTB-vRPyJniVQ0q804PPMw__epx1Ml6DBadH9FO2kX_ny2_AQ-yp5s</recordid><startdate>20090905</startdate><enddate>20090905</enddate><creator>Kumamoto, Hiroki</creator><creator>Haraguchi, Kazuhiro</creator><creator>Ida, Mayumi</creator><creator>Nakamura, Kazuo T.</creator><creator>Kitagawa, Yasuyuki</creator><creator>Hamasaki, Takayuki</creator><creator>Baba, Masanori</creator><creator>Matsubayashi, Satoko Shimbara</creator><creator>Tanaka, Hiromichi</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>20090905</creationdate><title>Synthesis of (±)-4′-ethynyl-5′,5′-difluoro-2′,3′-dehydro-3′-deoxy- carbocyclic thymidine: a difluoromethylidene analogue of promising anti-HIV agent Ed4T</title><author>Kumamoto, Hiroki ; Haraguchi, Kazuhiro ; Ida, Mayumi ; Nakamura, Kazuo T. ; Kitagawa, Yasuyuki ; Hamasaki, Takayuki ; Baba, Masanori ; Matsubayashi, Satoko Shimbara ; Tanaka, Hiromichi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c358t-e687888d5333de39b0bd932e224831f378d36818f2b549b7b9f454c7b4b699813</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Antibiotics. 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Drug treatments</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kumamoto, Hiroki</creatorcontrib><creatorcontrib>Haraguchi, Kazuhiro</creatorcontrib><creatorcontrib>Ida, Mayumi</creatorcontrib><creatorcontrib>Nakamura, Kazuo T.</creatorcontrib><creatorcontrib>Kitagawa, Yasuyuki</creatorcontrib><creatorcontrib>Hamasaki, Takayuki</creatorcontrib><creatorcontrib>Baba, Masanori</creatorcontrib><creatorcontrib>Matsubayashi, Satoko Shimbara</creatorcontrib><creatorcontrib>Tanaka, Hiromichi</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kumamoto, Hiroki</au><au>Haraguchi, Kazuhiro</au><au>Ida, Mayumi</au><au>Nakamura, Kazuo T.</au><au>Kitagawa, Yasuyuki</au><au>Hamasaki, Takayuki</au><au>Baba, Masanori</au><au>Matsubayashi, Satoko Shimbara</au><au>Tanaka, Hiromichi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of (±)-4′-ethynyl-5′,5′-difluoro-2′,3′-dehydro-3′-deoxy- carbocyclic thymidine: a difluoromethylidene analogue of promising anti-HIV agent Ed4T</atitle><jtitle>Tetrahedron</jtitle><date>2009-09-05</date><risdate>2009</risdate><volume>65</volume><issue>36</issue><spage>7630</spage><epage>7636</epage><pages>7630-7636</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>Synthesis of (±)-4′-ethynyl-5′,5′-difluoro-2′,3′-dehydro-3′-deoxy-carbocyclic-thymidine (
8) was carried out. The difluoromethylylidene group of
8 was constructed by the electrophilic fluorination to the cyclopentenone
11 by using Selectfluor
®. Introduction of thymine base was investigated based on the Mitsunobu reaction by employing cyclopentenyl allyl alcohols variously substituted at the 4-position. It was found the 4-methoxycarbonyl derivative
14 gave the highest selectivity both in terms of regio- and stereochemistry.
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| ispartof | Tetrahedron, 2009-09, Vol.65 (36), p.7630-7636 |
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| language | eng |
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| source | ScienceDirect Freedom Collection |
| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Biological and medical sciences Carbocyclic nucleoside Carbohydrates. Nucleosides and nucleotides Chemistry d4T Exact sciences and technology gem-Difluoromethylidene Human immunodeficiency virus Medical sciences Mitsunobu reaction Nucleosides, nucleotides and oligonucleotides Organic chemistry Pharmacology. Drug treatments Preparations and properties |
| title | Synthesis of (±)-4′-ethynyl-5′,5′-difluoro-2′,3′-dehydro-3′-deoxy- carbocyclic thymidine: a difluoromethylidene analogue of promising anti-HIV agent Ed4T |
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