A Facile Synthesis of 3β,25-dihydroxy-5α-Cholest-7-ene, the Precursor to HMG-CoA Reductase Inhibitor
An efficient four-step procedure is described for the synthesis of 3β,25-dihydroxy-5α-cholest-7-ene from 3β-hydroxy-5α-cholesta-7,24-diene in an overall yield of 34%. This product can serve as a precursor for the synthesis of an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase. The 3β-to...
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| Veröffentlicht in: | Journal of chemical research 2018-03, Vol.42 (3), p.156-159 |
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| creator | Jin, Can Liao, Zhibing Sun, Bin Xu, Tengwei |
| description | An efficient four-step procedure is described for the synthesis of 3β,25-dihydroxy-5α-cholest-7-ene from 3β-hydroxy-5α-cholesta-7,24-diene in an overall yield of 34%. This product can serve as a precursor for the synthesis of an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase. The 3β-toluene-p-sulfonate ester of 5α-cholesta-7,24-diene was obtained from natural lanolin followed by treatment with toluene-p-sulfonyl chloride. The key step in the synthesis is a very mild method for the hydroxybromination of this ester with N-bromosuccinimide in water, followed by reduction with LiAlH4 to obtain the 3β-toluene-p-sulfonate ester of 25-hydroxy-5α-cholesta-7-ene. The final product was obtained after desulfonation of 3β-toluene-p-sulfonyoxy-25-hydroxy-5α-cholesta-7-ene to afford 3β,25-dihydroxy-5α-cholest-7-ene in excellent yield. The reagents are all relatively cheap, non-toxic and stable. |
| doi_str_mv | 10.3184/174751918X15220628915420 |
| format | Article |
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This product can serve as a precursor for the synthesis of an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase. The 3β-toluene-p-sulfonate ester of 5α-cholesta-7,24-diene was obtained from natural lanolin followed by treatment with toluene-p-sulfonyl chloride. The key step in the synthesis is a very mild method for the hydroxybromination of this ester with N-bromosuccinimide in water, followed by reduction with LiAlH4 to obtain the 3β-toluene-p-sulfonate ester of 25-hydroxy-5α-cholesta-7-ene. The final product was obtained after desulfonation of 3β-toluene-p-sulfonyoxy-25-hydroxy-5α-cholesta-7-ene to afford 3β,25-dihydroxy-5α-cholest-7-ene in excellent yield. The reagents are all relatively cheap, non-toxic and stable.</description><identifier>ISSN: 1747-5198</identifier><identifier>EISSN: 2047-6507</identifier><identifier>DOI: 10.3184/174751918X15220628915420</identifier><language>eng</language><publisher>London, England: SAGE Publications</publisher><subject>Inhibitors ; Lanolin ; Lithium aluminum hydrides ; Precursors ; Reagents ; Statins ; Synthesis ; Toluene</subject><ispartof>Journal of chemical research, 2018-03, Vol.42 (3), p.156-159</ispartof><rights>2018 SAGE Publications</rights><rights>Copyright Science Reviews 2000 Ltd Mar 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c278t-a674db9106ba472404f7ad976d96ac2e23599896587d7a2141b6a9c76371b6e13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://journals.sagepub.com/doi/pdf/10.3184/174751918X15220628915420$$EPDF$$P50$$Gsage$$H</linktopdf><linktohtml>$$Uhttps://journals.sagepub.com/doi/10.3184/174751918X15220628915420$$EHTML$$P50$$Gsage$$H</linktohtml><link.rule.ids>314,776,780,21946,27832,27903,27904,44924,45312</link.rule.ids><linktorsrc>$$Uhttps://journals.sagepub.com/doi/full/10.3184/174751918X15220628915420?utm_source=summon&utm_medium=discovery-provider$$EView_record_in_SAGE_Publications$$FView_record_in_$$GSAGE_Publications</linktorsrc></links><search><creatorcontrib>Jin, Can</creatorcontrib><creatorcontrib>Liao, Zhibing</creatorcontrib><creatorcontrib>Sun, Bin</creatorcontrib><creatorcontrib>Xu, Tengwei</creatorcontrib><title>A Facile Synthesis of 3β,25-dihydroxy-5α-Cholest-7-ene, the Precursor to HMG-CoA Reductase Inhibitor</title><title>Journal of chemical research</title><description>An efficient four-step procedure is described for the synthesis of 3β,25-dihydroxy-5α-cholest-7-ene from 3β-hydroxy-5α-cholesta-7,24-diene in an overall yield of 34%. This product can serve as a precursor for the synthesis of an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase. The 3β-toluene-p-sulfonate ester of 5α-cholesta-7,24-diene was obtained from natural lanolin followed by treatment with toluene-p-sulfonyl chloride. The key step in the synthesis is a very mild method for the hydroxybromination of this ester with N-bromosuccinimide in water, followed by reduction with LiAlH4 to obtain the 3β-toluene-p-sulfonate ester of 25-hydroxy-5α-cholesta-7-ene. The final product was obtained after desulfonation of 3β-toluene-p-sulfonyoxy-25-hydroxy-5α-cholesta-7-ene to afford 3β,25-dihydroxy-5α-cholest-7-ene in excellent yield. The reagents are all relatively cheap, non-toxic and stable.</description><subject>Inhibitors</subject><subject>Lanolin</subject><subject>Lithium aluminum hydrides</subject><subject>Precursors</subject><subject>Reagents</subject><subject>Statins</subject><subject>Synthesis</subject><subject>Toluene</subject><issn>1747-5198</issn><issn>2047-6507</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNqFkMtKxDAUhoMoOI6-Q8DtRJM01-VQnAuMKF7AXUnb1HYYmzFpwT6WPsg8kxlGcCWuzll8_3cOPwCQ4KuEKHZNJJOcaKJeCKcUC6o04YziIzCimEkkOJbHYLTHUOTUKTgLYY0x40KTEaimcGaKZmPh49B2tQ1NgK6Cye5rQjkqm3oovfsYEN99orR2Gxs6JJFt7QRGGt57W_Q-OA87Bxe3c5S6KXywZV90Jli4bOsmbzrnz8FJZTbBXvzMMXie3TylC7S6my_T6QoVVKoOGSFZmWuCRW6YpAyzSppSS1FqYQpqacK1VlpwJUtpKGEkF0YXUiQybpYkY3B58G69e-_js9na9b6NJzOKKVN7tY6UOlCFdyF4W2Vb37wZP2QEZ_tWs79ajVF-iAbzan_l_-a-AXdfd90</recordid><startdate>201803</startdate><enddate>201803</enddate><creator>Jin, Can</creator><creator>Liao, Zhibing</creator><creator>Sun, Bin</creator><creator>Xu, Tengwei</creator><general>SAGE Publications</general><general>Sage Publications Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>EHMNL</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope></search><sort><creationdate>201803</creationdate><title>A Facile Synthesis of 3β,25-dihydroxy-5α-Cholest-7-ene, the Precursor to HMG-CoA Reductase Inhibitor</title><author>Jin, Can ; Liao, Zhibing ; Sun, Bin ; Xu, Tengwei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c278t-a674db9106ba472404f7ad976d96ac2e23599896587d7a2141b6a9c76371b6e13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Inhibitors</topic><topic>Lanolin</topic><topic>Lithium aluminum hydrides</topic><topic>Precursors</topic><topic>Reagents</topic><topic>Statins</topic><topic>Synthesis</topic><topic>Toluene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jin, Can</creatorcontrib><creatorcontrib>Liao, Zhibing</creatorcontrib><creatorcontrib>Sun, Bin</creatorcontrib><creatorcontrib>Xu, Tengwei</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>UK & Ireland Database</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><jtitle>Journal of chemical research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>Jin, Can</au><au>Liao, Zhibing</au><au>Sun, Bin</au><au>Xu, Tengwei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Facile Synthesis of 3β,25-dihydroxy-5α-Cholest-7-ene, the Precursor to HMG-CoA Reductase Inhibitor</atitle><jtitle>Journal of chemical research</jtitle><date>2018-03</date><risdate>2018</risdate><volume>42</volume><issue>3</issue><spage>156</spage><epage>159</epage><pages>156-159</pages><issn>1747-5198</issn><eissn>2047-6507</eissn><abstract>An efficient four-step procedure is described for the synthesis of 3β,25-dihydroxy-5α-cholest-7-ene from 3β-hydroxy-5α-cholesta-7,24-diene in an overall yield of 34%. This product can serve as a precursor for the synthesis of an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase. The 3β-toluene-p-sulfonate ester of 5α-cholesta-7,24-diene was obtained from natural lanolin followed by treatment with toluene-p-sulfonyl chloride. The key step in the synthesis is a very mild method for the hydroxybromination of this ester with N-bromosuccinimide in water, followed by reduction with LiAlH4 to obtain the 3β-toluene-p-sulfonate ester of 25-hydroxy-5α-cholesta-7-ene. The final product was obtained after desulfonation of 3β-toluene-p-sulfonyoxy-25-hydroxy-5α-cholesta-7-ene to afford 3β,25-dihydroxy-5α-cholest-7-ene in excellent yield. The reagents are all relatively cheap, non-toxic and stable.</abstract><cop>London, England</cop><pub>SAGE Publications</pub><doi>10.3184/174751918X15220628915420</doi><tpages>4</tpages></addata></record> |
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| source | Sage Journals GOLD Open Access 2024 |
| subjects | Inhibitors Lanolin Lithium aluminum hydrides Precursors Reagents Statins Synthesis Toluene |
| title | A Facile Synthesis of 3β,25-dihydroxy-5α-Cholest-7-ene, the Precursor to HMG-CoA Reductase Inhibitor |
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