Synthesis of (19E)-3 beta,7 alpha-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, a new hapten for 7 alpha-hydroxydehydroepiandrosterone (3 beta,7 alpha-dihydroxyandrost-5-en-17-one)
The title compound was prepared in 11 steps from 17,17-ethylenedioxy-19-hydroxyandrost-5-en-3 beta-yl acetate. After tert-butyldimethylsilyl protection of the 19-hydroxyl group, a 7-oxo group was introduced by oxidation with 3,5-dimethylpyrazole-chromium trioxide complex, and then selectively reduce...
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| Veröffentlicht in: | Steroids 1998-09, Vol.63 (9), p.454-458 |
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| container_title | Steroids |
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| creator | Pouzar, V Slavíková, T Cerńy, I |
| description | The title compound was prepared in 11 steps from 17,17-ethylenedioxy-19-hydroxyandrost-5-en-3 beta-yl acetate. After tert-butyldimethylsilyl protection of the 19-hydroxyl group, a 7-oxo group was introduced by oxidation with 3,5-dimethylpyrazole-chromium trioxide complex, and then selectively reduced with L-Selectride to give a 7 alpha-hydroxy derivative. This partially protected triol was acetylated and desilylated to 3,7-diacetate. Subsequent oxidation with pyridine-chromium trioxide complex gave 19-aldehyde, which was transformed into the corresponding protected 19-(O-carboxymethyl)oxime. Successive ketal cleavage, deacetylation, and methyl ester splitting gave the final (19E)-3 beta,7 alpha-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, designed as a hapten for 7 alpha-hydroxydehydroepiandrosterone immunoassays. |
| doi_str_mv | 10.1016/S0039-128X(98)00047-6 |
| format | Article |
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After tert-butyldimethylsilyl protection of the 19-hydroxyl group, a 7-oxo group was introduced by oxidation with 3,5-dimethylpyrazole-chromium trioxide complex, and then selectively reduced with L-Selectride to give a 7 alpha-hydroxy derivative. This partially protected triol was acetylated and desilylated to 3,7-diacetate. Subsequent oxidation with pyridine-chromium trioxide complex gave 19-aldehyde, which was transformed into the corresponding protected 19-(O-carboxymethyl)oxime. Successive ketal cleavage, deacetylation, and methyl ester splitting gave the final (19E)-3 beta,7 alpha-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, designed as a hapten for 7 alpha-hydroxydehydroepiandrosterone immunoassays.</description><identifier>ISSN: 0039-128X</identifier><identifier>DOI: 10.1016/S0039-128X(98)00047-6</identifier><identifier>PMID: 9727091</identifier><language>eng</language><publisher>United States</publisher><subject>Androstenols - chemical synthesis ; Androstenols - chemistry ; Dehydroepiandrosterone - analogs & derivatives ; Dehydroepiandrosterone - chemistry ; Haptens - chemistry ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Oximes - chemical synthesis ; Oximes - chemistry</subject><ispartof>Steroids, 1998-09, Vol.63 (9), p.454-458</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9727091$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pouzar, V</creatorcontrib><creatorcontrib>Slavíková, T</creatorcontrib><creatorcontrib>Cerńy, I</creatorcontrib><title>Synthesis of (19E)-3 beta,7 alpha-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, a new hapten for 7 alpha-hydroxydehydroepiandrosterone (3 beta,7 alpha-dihydroxyandrost-5-en-17-one)</title><title>Steroids</title><addtitle>Steroids</addtitle><description>The title compound was prepared in 11 steps from 17,17-ethylenedioxy-19-hydroxyandrost-5-en-3 beta-yl acetate. After tert-butyldimethylsilyl protection of the 19-hydroxyl group, a 7-oxo group was introduced by oxidation with 3,5-dimethylpyrazole-chromium trioxide complex, and then selectively reduced with L-Selectride to give a 7 alpha-hydroxy derivative. This partially protected triol was acetylated and desilylated to 3,7-diacetate. Subsequent oxidation with pyridine-chromium trioxide complex gave 19-aldehyde, which was transformed into the corresponding protected 19-(O-carboxymethyl)oxime. Successive ketal cleavage, deacetylation, and methyl ester splitting gave the final (19E)-3 beta,7 alpha-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, designed as a hapten for 7 alpha-hydroxydehydroepiandrosterone immunoassays.</description><subject>Androstenols - chemical synthesis</subject><subject>Androstenols - chemistry</subject><subject>Dehydroepiandrosterone - analogs & derivatives</subject><subject>Dehydroepiandrosterone - chemistry</subject><subject>Haptens - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Oximes - chemical synthesis</subject><subject>Oximes - chemistry</subject><issn>0039-128X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kMtKw0AUhmeh1Fp9hMKspIGOziXNZJZS6gWELqrgLkwyJySSzMRMis37-WCGGgUXbs715zs_B6E5o9eMsuhmR6lQhPH4daHigFIaShKdoOnv-Ayde_82LCKh-ARNlOSSKjZFn7vedgX40mOX4wVTm4AInEKnlxLrqik0MWXRm9YdesIkcQen7dD5jqwIWMIU0RUe4mJLMt2mg6yGruirwB3KGpZYYwsfuNBNBxbnrsU_2BFq4FhAU45caJ0FvPjPxN_rgyELwQU6zXXl4XLMM_Ryt3leP5Cn7f3j-vaJNEzEHYmkABMJqSiomGsRchWzTLIsMzyNVZZGZiV5yk260kzkWR7pnKYsDCNDtYmVmKGrb27Tuvc9-C6pS59BVWkLbu8TOTxXyqNwPgr3aQ0madqy1m2fjG8XX7SphE8</recordid><startdate>199809</startdate><enddate>199809</enddate><creator>Pouzar, V</creator><creator>Slavíková, T</creator><creator>Cerńy, I</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>199809</creationdate><title>Synthesis of (19E)-3 beta,7 alpha-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, a new hapten for 7 alpha-hydroxydehydroepiandrosterone (3 beta,7 alpha-dihydroxyandrost-5-en-17-one)</title><author>Pouzar, V ; Slavíková, T ; Cerńy, I</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p138t-673ed63790e982a342981c71ccd2b89cb6d572b2db5a13fcf6af0b1446d0ad893</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>Androstenols - chemical synthesis</topic><topic>Androstenols - chemistry</topic><topic>Dehydroepiandrosterone - analogs & derivatives</topic><topic>Dehydroepiandrosterone - chemistry</topic><topic>Haptens - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Oximes - chemical synthesis</topic><topic>Oximes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pouzar, V</creatorcontrib><creatorcontrib>Slavíková, T</creatorcontrib><creatorcontrib>Cerńy, I</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pouzar, V</au><au>Slavíková, T</au><au>Cerńy, I</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of (19E)-3 beta,7 alpha-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, a new hapten for 7 alpha-hydroxydehydroepiandrosterone (3 beta,7 alpha-dihydroxyandrost-5-en-17-one)</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>1998-09</date><risdate>1998</risdate><volume>63</volume><issue>9</issue><spage>454</spage><epage>458</epage><pages>454-458</pages><issn>0039-128X</issn><abstract>The title compound was prepared in 11 steps from 17,17-ethylenedioxy-19-hydroxyandrost-5-en-3 beta-yl acetate. After tert-butyldimethylsilyl protection of the 19-hydroxyl group, a 7-oxo group was introduced by oxidation with 3,5-dimethylpyrazole-chromium trioxide complex, and then selectively reduced with L-Selectride to give a 7 alpha-hydroxy derivative. This partially protected triol was acetylated and desilylated to 3,7-diacetate. Subsequent oxidation with pyridine-chromium trioxide complex gave 19-aldehyde, which was transformed into the corresponding protected 19-(O-carboxymethyl)oxime. Successive ketal cleavage, deacetylation, and methyl ester splitting gave the final (19E)-3 beta,7 alpha-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, designed as a hapten for 7 alpha-hydroxydehydroepiandrosterone immunoassays.</abstract><cop>United States</cop><pmid>9727091</pmid><doi>10.1016/S0039-128X(98)00047-6</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0039-128X |
| ispartof | Steroids, 1998-09, Vol.63 (9), p.454-458 |
| issn | 0039-128X |
| language | eng |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Androstenols - chemical synthesis Androstenols - chemistry Dehydroepiandrosterone - analogs & derivatives Dehydroepiandrosterone - chemistry Haptens - chemistry Magnetic Resonance Spectroscopy Molecular Structure Oximes - chemical synthesis Oximes - chemistry |
| title | Synthesis of (19E)-3 beta,7 alpha-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, a new hapten for 7 alpha-hydroxydehydroepiandrosterone (3 beta,7 alpha-dihydroxyandrost-5-en-17-one) |
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