Synthesis of a Key Intermediate for the Preparation of FTY720 Analogs
A concise synthesis of a useful intermediate 10 for the preparation of fingolimod (FTY-720) analogs was achieved by utilizing a chemoselective Sonogashira reaction of trihalobenzene 12 with alkyne 13. The reaction proceeded with high selectivity to give alkyne 11 containing the dihalobenzene moiety...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2012/11/01, Vol.60(11), pp.1395-1398 |
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| container_end_page | 1398 |
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| container_issue | 11 |
| container_start_page | 1395 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 60 |
| creator | Hamada, Maiko Adachi, Kunitomo Hikawa, Hidemasa Yokoyama, Yuusaku |
| description | A concise synthesis of a useful intermediate 10 for the preparation of fingolimod (FTY-720) analogs was achieved by utilizing a chemoselective Sonogashira reaction of trihalobenzene 12 with alkyne 13. The reaction proceeded with high selectivity to give alkyne 11 containing the dihalobenzene moiety in good yield. Compound 11 was converted into intermediate 10 by hydrogenation without reduction of the halogen atoms. |
| doi_str_mv | 10.1248/cpb.c12-00477 |
| format | Article |
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Adachi, Kunitomo ; Hikawa, Hidemasa ; Yokoyama, Yuusaku</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c679t-938e72ca2fa057cf125ead66b24f7e5a489b9b558eec678f5bf38ce179afe103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alkynes - chemical synthesis</topic><topic>Alkynes - chemistry</topic><topic>Benzene Derivatives - chemical synthesis</topic><topic>Benzene Derivatives - chemistry</topic><topic>Catalysis</topic><topic>chemoselectivity</topic><topic>cross-coupling</topic><topic>fingolimod</topic><topic>Fingolimod Hydrochloride</topic><topic>Immunosuppressive Agents - chemical synthesis</topic><topic>Immunosuppressive Agents - chemistry</topic><topic>KRP-203</topic><topic>palladium</topic><topic>Palladium - chemistry</topic><topic>Propylene Glycols - chemical synthesis</topic><topic>Propylene Glycols - chemistry</topic><topic>Sphingosine - analogs & derivatives</topic><topic>Sphingosine - chemical synthesis</topic><topic>Sphingosine - chemistry</topic><topic>Sulfhydryl Compounds - chemical synthesis</topic><topic>Sulfhydryl Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hamada, Maiko</creatorcontrib><creatorcontrib>Adachi, Kunitomo</creatorcontrib><creatorcontrib>Hikawa, Hidemasa</creatorcontrib><creatorcontrib>Yokoyama, Yuusaku</creatorcontrib><creatorcontrib>School of Pharmaceutical Science</creatorcontrib><creatorcontrib>Research Division</creatorcontrib><creatorcontrib>Toho University</creatorcontrib><creatorcontrib>Medicinal Chemistry Research Laboratories I</creatorcontrib><creatorcontrib>Mitsubishi Tanabe Pharma Corporation</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hamada, Maiko</au><au>Adachi, Kunitomo</au><au>Hikawa, Hidemasa</au><au>Yokoyama, Yuusaku</au><aucorp>School of Pharmaceutical Science</aucorp><aucorp>Research Division</aucorp><aucorp>Toho University</aucorp><aucorp>Medicinal Chemistry Research Laboratories I</aucorp><aucorp>Mitsubishi Tanabe Pharma Corporation</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of a Key Intermediate for the Preparation of FTY720 Analogs</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2012-11-01</date><risdate>2012</risdate><volume>60</volume><issue>11</issue><spage>1395</spage><epage>1398</epage><pages>1395-1398</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>A concise synthesis of a useful intermediate 10 for the preparation of fingolimod (FTY-720) analogs was achieved by utilizing a chemoselective Sonogashira reaction of trihalobenzene 12 with alkyne 13. The reaction proceeded with high selectivity to give alkyne 11 containing the dihalobenzene moiety in good yield. Compound 11 was converted into intermediate 10 by hydrogenation without reduction of the halogen atoms.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>23124563</pmid><doi>10.1248/cpb.c12-00477</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 2012/11/01, Vol.60(11), pp.1395-1398 |
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| source | J-STAGE Free; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | Alkynes - chemical synthesis Alkynes - chemistry Benzene Derivatives - chemical synthesis Benzene Derivatives - chemistry Catalysis chemoselectivity cross-coupling fingolimod Fingolimod Hydrochloride Immunosuppressive Agents - chemical synthesis Immunosuppressive Agents - chemistry KRP-203 palladium Palladium - chemistry Propylene Glycols - chemical synthesis Propylene Glycols - chemistry Sphingosine - analogs & derivatives Sphingosine - chemical synthesis Sphingosine - chemistry Sulfhydryl Compounds - chemical synthesis Sulfhydryl Compounds - chemistry |
| title | Synthesis of a Key Intermediate for the Preparation of FTY720 Analogs |
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