Preparation of Optically Pure δ-Lactones Using Diastereomeric Resolution with Amino Acid as Resolving Agent
Synthesis of optically pure δ-lactones by diastereomeric resolution was investigated. Amino acid derivatives, which can be obtained at a relatively low cost, were used as resolving agents. Six optically pure δ-lactones were efficiently synthesized using Cbz-L-alanine without other expensive resolvin...
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| Veröffentlicht in: | Journal of Oleo Science 2015, Vol.64(1), pp.75-90 |
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| container_end_page | 90 |
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| container_issue | 1 |
| container_start_page | 75 |
| container_title | Journal of Oleo Science |
| container_volume | 64 |
| creator | Shimotori, Yasutaka Hoshi, Masayuki Seki, Syota Osanai, Takeshi Okabe, Hayato Ikeda, Yoshitaka Miyakoshi, Tetsuo |
| description | Synthesis of optically pure δ-lactones by diastereomeric resolution was investigated. Amino acid derivatives, which can be obtained at a relatively low cost, were used as resolving agents. Six optically pure δ-lactones were efficiently synthesized using Cbz-L-alanine without other expensive resolving agents. Both enantiomers of δ-lactone obtained had over 98% enantiomeric excesses. This diastereomeric resolution is very efficient for the preparation of optically pure δ-lactones. |
| doi_str_mv | 10.5650/jos.ess14124 |
| format | Article |
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Amino acid derivatives, which can be obtained at a relatively low cost, were used as resolving agents. Six optically pure δ-lactones were efficiently synthesized using Cbz-L-alanine without other expensive resolving agents. Both enantiomers of δ-lactone obtained had over 98% enantiomeric excesses. This diastereomeric resolution is very efficient for the preparation of optically pure δ-lactones.</description><identifier>ISSN: 1345-8957</identifier><identifier>EISSN: 1347-3352</identifier><identifier>DOI: 10.5650/jos.ess14124</identifier><identifier>PMID: 25742924</identifier><language>eng</language><publisher>Japan: Japan Oil Chemists' Society</publisher><subject>Alanine - analogs & derivatives ; Alanine - chemistry ; amino acid ; Amino acids ; Amino Acids - chemistry ; Derivatives ; diastereomeric resolution ; Enantiomers ; Lactones - chemical synthesis ; Low cost ; resolving agent ; Stereoisomerism ; Synthesis ; δ-lactone</subject><ispartof>Journal of Oleo Science, 2015, Vol.64(1), pp.75-90</ispartof><rights>2015 by Japan Oil Chemists' Society</rights><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c487t-3be72de4a2c332b0bb99c63a282131a1b9c181c353f9177a20050eece54bd33e3</citedby><cites>FETCH-LOGICAL-c487t-3be72de4a2c332b0bb99c63a282131a1b9c181c353f9177a20050eece54bd33e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1876,4009,27902,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25742924$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shimotori, Yasutaka</creatorcontrib><creatorcontrib>Hoshi, Masayuki</creatorcontrib><creatorcontrib>Seki, Syota</creatorcontrib><creatorcontrib>Osanai, Takeshi</creatorcontrib><creatorcontrib>Okabe, Hayato</creatorcontrib><creatorcontrib>Ikeda, Yoshitaka</creatorcontrib><creatorcontrib>Miyakoshi, Tetsuo</creatorcontrib><title>Preparation of Optically Pure δ-Lactones Using Diastereomeric Resolution with Amino Acid as Resolving Agent</title><title>Journal of Oleo Science</title><addtitle>J Oleo Sci</addtitle><description>Synthesis of optically pure δ-lactones by diastereomeric resolution was investigated. Amino acid derivatives, which can be obtained at a relatively low cost, were used as resolving agents. Six optically pure δ-lactones were efficiently synthesized using Cbz-L-alanine without other expensive resolving agents. Both enantiomers of δ-lactone obtained had over 98% enantiomeric excesses. This diastereomeric resolution is very efficient for the preparation of optically pure δ-lactones.</description><subject>Alanine - analogs & derivatives</subject><subject>Alanine - chemistry</subject><subject>amino acid</subject><subject>Amino acids</subject><subject>Amino Acids - chemistry</subject><subject>Derivatives</subject><subject>diastereomeric resolution</subject><subject>Enantiomers</subject><subject>Lactones - chemical synthesis</subject><subject>Low cost</subject><subject>resolving agent</subject><subject>Stereoisomerism</subject><subject>Synthesis</subject><subject>δ-lactone</subject><issn>1345-8957</issn><issn>1347-3352</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kM9OGzEQh62qqElpbz1XPvbAgv_Gu8eUloIUCYTI2fI6k8TR7jr1eKl4L56jz8QmIbnMjGa--R0-Qr5xdqknml1tIl4CIldcqA9kzKUyhZRafNzPuigrbUbkM-KGsWGvzScyEtooUQk1Js1Dgq1LLofY0bik99scvGuaF_rQJ6D_X4uZ8zl2gHSOoVvRX8FhhgSxhRQ8fQSMTb___hfymk7b0EU69WFBHR6uz7u36Qq6_IWcLV2D8PW9n5P5ze-n69tidv_n7no6K7wqTS5kDUYsQDnhpRQ1q-uq8hPpRCm45I7Xlecl91LLZcWNcYIxzQA8aFUvpAR5Tn4ccrcp_u0Bs20Demga10Hs0fKSMTWRxlQDenFAfYqICZZ2m0Lr0ovlzO782sGvPfod8O_vyX3dwuIEH4UOwM8DsMHsVnACXBq8NrBPmyjLd-WYejr6tUsWOvkGgHCREQ</recordid><startdate>2015</startdate><enddate>2015</enddate><creator>Shimotori, Yasutaka</creator><creator>Hoshi, Masayuki</creator><creator>Seki, Syota</creator><creator>Osanai, Takeshi</creator><creator>Okabe, Hayato</creator><creator>Ikeda, Yoshitaka</creator><creator>Miyakoshi, Tetsuo</creator><general>Japan Oil Chemists' Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>8FD</scope><scope>F28</scope><scope>FR3</scope></search><sort><creationdate>2015</creationdate><title>Preparation of Optically Pure δ-Lactones Using Diastereomeric Resolution with Amino Acid as Resolving Agent</title><author>Shimotori, Yasutaka ; Hoshi, Masayuki ; Seki, Syota ; Osanai, Takeshi ; Okabe, Hayato ; Ikeda, Yoshitaka ; Miyakoshi, Tetsuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c487t-3be72de4a2c332b0bb99c63a282131a1b9c181c353f9177a20050eece54bd33e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alanine - analogs & derivatives</topic><topic>Alanine - chemistry</topic><topic>amino acid</topic><topic>Amino acids</topic><topic>Amino Acids - chemistry</topic><topic>Derivatives</topic><topic>diastereomeric resolution</topic><topic>Enantiomers</topic><topic>Lactones - chemical synthesis</topic><topic>Low cost</topic><topic>resolving agent</topic><topic>Stereoisomerism</topic><topic>Synthesis</topic><topic>δ-lactone</topic><toplevel>online_resources</toplevel><creatorcontrib>Shimotori, Yasutaka</creatorcontrib><creatorcontrib>Hoshi, Masayuki</creatorcontrib><creatorcontrib>Seki, Syota</creatorcontrib><creatorcontrib>Osanai, Takeshi</creatorcontrib><creatorcontrib>Okabe, Hayato</creatorcontrib><creatorcontrib>Ikeda, Yoshitaka</creatorcontrib><creatorcontrib>Miyakoshi, Tetsuo</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><jtitle>Journal of Oleo Science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shimotori, Yasutaka</au><au>Hoshi, Masayuki</au><au>Seki, Syota</au><au>Osanai, Takeshi</au><au>Okabe, Hayato</au><au>Ikeda, Yoshitaka</au><au>Miyakoshi, Tetsuo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation of Optically Pure δ-Lactones Using Diastereomeric Resolution with Amino Acid as Resolving Agent</atitle><jtitle>Journal of Oleo Science</jtitle><addtitle>J Oleo Sci</addtitle><date>2015</date><risdate>2015</risdate><volume>64</volume><issue>1</issue><spage>75</spage><epage>90</epage><pages>75-90</pages><issn>1345-8957</issn><eissn>1347-3352</eissn><abstract>Synthesis of optically pure δ-lactones by diastereomeric resolution was investigated. Amino acid derivatives, which can be obtained at a relatively low cost, were used as resolving agents. Six optically pure δ-lactones were efficiently synthesized using Cbz-L-alanine without other expensive resolving agents. Both enantiomers of δ-lactone obtained had over 98% enantiomeric excesses. This diastereomeric resolution is very efficient for the preparation of optically pure δ-lactones.</abstract><cop>Japan</cop><pub>Japan Oil Chemists' Society</pub><pmid>25742924</pmid><doi>10.5650/jos.ess14124</doi><tpages>16</tpages><oa>free_for_read</oa></addata></record> |
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| source | J-STAGE Free; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | Alanine - analogs & derivatives Alanine - chemistry amino acid Amino acids Amino Acids - chemistry Derivatives diastereomeric resolution Enantiomers Lactones - chemical synthesis Low cost resolving agent Stereoisomerism Synthesis δ-lactone |
| title | Preparation of Optically Pure δ-Lactones Using Diastereomeric Resolution with Amino Acid as Resolving Agent |
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