Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using ( S)-2-methoxy-2-(1-naphthyl)propionic acid
To investigate the resolution of secondary alcohols using 2-methoxy-2-(1-naphthyl)propionic acid (MαNP acid), 2-methyl-4-heptanol, one of the aggregation pheromones of Metamasius hemipterus, was resolved using ( S)-MαNP acid. As a chiral-resolving agent, MαNP acid is superior to 3,3,3-trifluoro-2-me...
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| Veröffentlicht in: | Journal of Chromatography A 2006-06, Vol.1117 (1), p.38-46 |
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| creator | Ichikawa, Akio Ono, Hiroshi |
| description | To investigate the resolution of secondary alcohols using 2-methoxy-2-(1-naphthyl)propionic acid (MαNP acid), 2-methyl-4-heptanol, one of the aggregation pheromones of
Metamasius hemipterus, was resolved using (
S)-MαNP acid. As a chiral-resolving agent, MαNP acid is superior to 3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (MTPA) in terms of HPLC separation and NMR shielding. A better separation of diastereomeric MαNP esters was observed when
n-hexane–THF was used as the eluent for silica gel HPLC. The solvolysis of the diastereomeric MαNP esters gave (
R)-2-methyl-4-heptanol and its enantiomer; enantiopure (
S)-MαNP acid was also recovered. In addition, the preferred conformation of the MαNP ester was confirmed using methyl (
R)-3-hydroxyvalerate as an authentic compound. |
| doi_str_mv | 10.1016/j.chroma.2006.03.100 |
| format | Article |
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Metamasius hemipterus, was resolved using (
S)-MαNP acid. As a chiral-resolving agent, MαNP acid is superior to 3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (MTPA) in terms of HPLC separation and NMR shielding. A better separation of diastereomeric MαNP esters was observed when
n-hexane–THF was used as the eluent for silica gel HPLC. The solvolysis of the diastereomeric MαNP esters gave (
R)-2-methyl-4-heptanol and its enantiomer; enantiopure (
S)-MαNP acid was also recovered. In addition, the preferred conformation of the MαNP ester was confirmed using methyl (
R)-3-hydroxyvalerate as an authentic compound.</description><identifier>ISSN: 0021-9673</identifier><identifier>DOI: 10.1016/j.chroma.2006.03.100</identifier><identifier>PMID: 16631765</identifier><identifier>CODEN: JOCRAM</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>2-Methoxy-2-(1-naphthyl)propionic acid ; Aliphatic compounds ; Analytical chemistry ; Animals ; Anisotropy ; Chemistry ; Chiral ; Chiral-resolving agent ; Chromatographic methods and physical methods associated with chromatography ; Coleoptera - chemistry ; Exact sciences and technology ; Heptanol - analogs & derivatives ; Heptanol - chemistry ; Naphthalenes - chemistry ; Organic chemistry ; Other chromatographic methods ; Pheromone ; Pheromones - chemistry ; Preparations and properties ; Propionates - chemistry ; Resolution ; Spectrum Analysis - methods ; Stereoisomerism ; Sulfhydryl Compounds</subject><ispartof>Journal of Chromatography A, 2006-06, Vol.1117 (1), p.38-46</ispartof><rights>2006 Elsevier B.V.</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c456t-22ab19ec1f0623d1a3aae43f437f0548a628af3c6c2c399f969c899e5abd56df3</citedby><cites>FETCH-LOGICAL-c456t-22ab19ec1f0623d1a3aae43f437f0548a628af3c6c2c399f969c899e5abd56df3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.chroma.2006.03.100$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17755541$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16631765$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ichikawa, Akio</creatorcontrib><creatorcontrib>Ono, Hiroshi</creatorcontrib><title>Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using ( S)-2-methoxy-2-(1-naphthyl)propionic acid</title><title>Journal of Chromatography A</title><addtitle>J Chromatogr A</addtitle><description>To investigate the resolution of secondary alcohols using 2-methoxy-2-(1-naphthyl)propionic acid (MαNP acid), 2-methyl-4-heptanol, one of the aggregation pheromones of
Metamasius hemipterus, was resolved using (
S)-MαNP acid. As a chiral-resolving agent, MαNP acid is superior to 3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (MTPA) in terms of HPLC separation and NMR shielding. A better separation of diastereomeric MαNP esters was observed when
n-hexane–THF was used as the eluent for silica gel HPLC. The solvolysis of the diastereomeric MαNP esters gave (
R)-2-methyl-4-heptanol and its enantiomer; enantiopure (
S)-MαNP acid was also recovered. In addition, the preferred conformation of the MαNP ester was confirmed using methyl (
R)-3-hydroxyvalerate as an authentic compound.</description><subject>2-Methoxy-2-(1-naphthyl)propionic acid</subject><subject>Aliphatic compounds</subject><subject>Analytical chemistry</subject><subject>Animals</subject><subject>Anisotropy</subject><subject>Chemistry</subject><subject>Chiral</subject><subject>Chiral-resolving agent</subject><subject>Chromatographic methods and physical methods associated with chromatography</subject><subject>Coleoptera - chemistry</subject><subject>Exact sciences and technology</subject><subject>Heptanol - analogs & derivatives</subject><subject>Heptanol - chemistry</subject><subject>Naphthalenes - chemistry</subject><subject>Organic chemistry</subject><subject>Other chromatographic methods</subject><subject>Pheromone</subject><subject>Pheromones - chemistry</subject><subject>Preparations and properties</subject><subject>Propionates - chemistry</subject><subject>Resolution</subject><subject>Spectrum Analysis - methods</subject><subject>Stereoisomerism</subject><subject>Sulfhydryl Compounds</subject><issn>0021-9673</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEGL1TAUhbtQnHH0H4hko8zA5Jk0TdpuBmRwRmFEQV2H-9Ibm0eb1KQV34_wP5vSB7NzlXD4zjmXUxSvONtxxtW7w870MYywKxlTOyayyp4U54yVnLaqFmfF85QOjPGa1eWz4owrJXit5Hnx92vECSLMLngSLEnO_xyQogefpREjKemIc38caEV7nGbwYbgmQKYec2PwuLo-4wwjJLck0uPophnjkq7JsqaRS_Ltim4p4c8x_y459TD1a-jVFMOUq50hYFz3onhqYUj48vReFD_uPny__Ugfvtx_un3_QE0l1UzLEva8RcMtU6XoOAgArIStRG2ZrBpQZQNWGGVKI9rWtqo1TduihH0nVWfFRfF2y831vxZMsx5dMjgM4DEsSau6VbLhTQarDTQxpBTR6im6EeJRc6bX6fVBb9PrdXrNRFZZtr0-5S_7EbtH02n3DLw5AZAMDDaCNy49cnUtpax45m42DvMavx1GnYxDb7BzEc2su-D-f8k_klGm_A</recordid><startdate>20060602</startdate><enddate>20060602</enddate><creator>Ichikawa, Akio</creator><creator>Ono, Hiroshi</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>IQODW</scope><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>7X8</scope></search><sort><creationdate>20060602</creationdate><title>Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using ( S)-2-methoxy-2-(1-naphthyl)propionic acid</title><author>Ichikawa, Akio ; Ono, Hiroshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c456t-22ab19ec1f0623d1a3aae43f437f0548a628af3c6c2c399f969c899e5abd56df3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>2-Methoxy-2-(1-naphthyl)propionic acid</topic><topic>Aliphatic compounds</topic><topic>Analytical chemistry</topic><topic>Animals</topic><topic>Anisotropy</topic><topic>Chemistry</topic><topic>Chiral</topic><topic>Chiral-resolving agent</topic><topic>Chromatographic methods and physical methods associated with chromatography</topic><topic>Coleoptera - chemistry</topic><topic>Exact sciences and technology</topic><topic>Heptanol - analogs & derivatives</topic><topic>Heptanol - chemistry</topic><topic>Naphthalenes - chemistry</topic><topic>Organic chemistry</topic><topic>Other chromatographic methods</topic><topic>Pheromone</topic><topic>Pheromones - chemistry</topic><topic>Preparations and properties</topic><topic>Propionates - chemistry</topic><topic>Resolution</topic><topic>Spectrum Analysis - methods</topic><topic>Stereoisomerism</topic><topic>Sulfhydryl Compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ichikawa, Akio</creatorcontrib><creatorcontrib>Ono, Hiroshi</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of Chromatography A</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ichikawa, Akio</au><au>Ono, Hiroshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using ( S)-2-methoxy-2-(1-naphthyl)propionic acid</atitle><jtitle>Journal of Chromatography A</jtitle><addtitle>J Chromatogr A</addtitle><date>2006-06-02</date><risdate>2006</risdate><volume>1117</volume><issue>1</issue><spage>38</spage><epage>46</epage><pages>38-46</pages><issn>0021-9673</issn><coden>JOCRAM</coden><abstract>To investigate the resolution of secondary alcohols using 2-methoxy-2-(1-naphthyl)propionic acid (MαNP acid), 2-methyl-4-heptanol, one of the aggregation pheromones of
Metamasius hemipterus, was resolved using (
S)-MαNP acid. As a chiral-resolving agent, MαNP acid is superior to 3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (MTPA) in terms of HPLC separation and NMR shielding. A better separation of diastereomeric MαNP esters was observed when
n-hexane–THF was used as the eluent for silica gel HPLC. The solvolysis of the diastereomeric MαNP esters gave (
R)-2-methyl-4-heptanol and its enantiomer; enantiopure (
S)-MαNP acid was also recovered. In addition, the preferred conformation of the MαNP ester was confirmed using methyl (
R)-3-hydroxyvalerate as an authentic compound.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>16631765</pmid><doi>10.1016/j.chroma.2006.03.100</doi><tpages>9</tpages></addata></record> |
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| language | eng |
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| subjects | 2-Methoxy-2-(1-naphthyl)propionic acid Aliphatic compounds Analytical chemistry Animals Anisotropy Chemistry Chiral Chiral-resolving agent Chromatographic methods and physical methods associated with chromatography Coleoptera - chemistry Exact sciences and technology Heptanol - analogs & derivatives Heptanol - chemistry Naphthalenes - chemistry Organic chemistry Other chromatographic methods Pheromone Pheromones - chemistry Preparations and properties Propionates - chemistry Resolution Spectrum Analysis - methods Stereoisomerism Sulfhydryl Compounds |
| title | Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using ( S)-2-methoxy-2-(1-naphthyl)propionic acid |
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