De Novo Synthesis of 4‘-Ethoxy Nucleoside Analogues
Butenolides 5a and 13 were used as optically active templates in the de novo synthesis of 4‘-disubstituted nucleoside analogues. The butenolides were reduced and acylated in situ to give acetates 10 and 14. Vorbrüggen coupling gave the protected nucleoside analogues 11 and 15. Reduction of 11 gave 4...
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| Veröffentlicht in: | Journal of organic chemistry 2002-11, Vol.67 (22), p.7649-7655 |
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| container_end_page | 7655 |
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| container_issue | 22 |
| container_start_page | 7649 |
| container_title | Journal of organic chemistry |
| container_volume | 67 |
| creator | Hegedus, Louis S Geisler, Lisa Riches, Andrew G Salman, Sarri S Umbricht, Gisela |
| description | Butenolides 5a and 13 were used as optically active templates in the de novo synthesis of 4‘-disubstituted nucleoside analogues. The butenolides were reduced and acylated in situ to give acetates 10 and 14. Vorbrüggen coupling gave the protected nucleoside analogues 11 and 15. Reduction of 11 gave 4‘-ethoxy-2‘,3‘-dideoxythymidine (6) and deprotection of 15 gave 4‘-ethoxy-2‘,3‘-dideoxydidehydrothymidine (7). The cis-dihydroxylation of a variety of butenolides occurred with the major product formed from oxidation of the β-face. |
| doi_str_mv | 10.1021/jo020151f |
| format | Article |
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The butenolides were reduced and acylated in situ to give acetates 10 and 14. Vorbrüggen coupling gave the protected nucleoside analogues 11 and 15. Reduction of 11 gave 4‘-ethoxy-2‘,3‘-dideoxythymidine (6) and deprotection of 15 gave 4‘-ethoxy-2‘,3‘-dideoxydidehydrothymidine (7). The cis-dihydroxylation of a variety of butenolides occurred with the major product formed from oxidation of the β-face.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo020151f</identifier><identifier>PMID: 12398485</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>4-Butyrolactone - analogs & derivatives ; Carbohydrates. 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Org. Chem</addtitle><description>Butenolides 5a and 13 were used as optically active templates in the de novo synthesis of 4‘-disubstituted nucleoside analogues. The butenolides were reduced and acylated in situ to give acetates 10 and 14. Vorbrüggen coupling gave the protected nucleoside analogues 11 and 15. Reduction of 11 gave 4‘-ethoxy-2‘,3‘-dideoxythymidine (6) and deprotection of 15 gave 4‘-ethoxy-2‘,3‘-dideoxydidehydrothymidine (7). The cis-dihydroxylation of a variety of butenolides occurred with the major product formed from oxidation of the β-face.</description><subject>4-Butyrolactone - analogs & derivatives</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Furans - chemistry</subject><subject>Hydroxylation</subject><subject>Molecular Structure</subject><subject>Nucleosides - chemical synthesis</subject><subject>Nucleosides - chemistry</subject><subject>Nucleosides, nucleotides and oligonucleotides</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtOAyEUBmBiNLZWF76AmY0mLka5DrBUWy9J4yWta8JQsKPTojBj7M7H8Pl8EjFt7EY2LPjyc84PwD6CJwhidPrsIYaIIbcBuohhmBcS0k3QhRDjnOCCdMBOjM8wHcbYNuggTKSggnUB69vs1r_7bLSYN1Mbq5h5l9Hvz6980Ez9xyK7bU1tfawmNjub69o_tTbugi2n62j3VncPPF4OxhfX-fDu6ubibJhrwmWTGz1xouSiZIxbpEsiS6IdJVCURjqBBcfCJGFMGkdMrBSo0MJQJyBlllvSA0fL3Nfg39K_jZpV0di61nPr26h42g0WmCd4vIQm-BiDdeo1VDMdFgpB9duR-uso2YNVaFvO7GQtV6UkcLgCOhpdu6DnpoprR4XkRNLk8qWrYmM__t51eFEFJ5yp8f1I9WFxefVwTtX1OlebmOZpQ6oz_jPgD_fgiOw</recordid><startdate>20021101</startdate><enddate>20021101</enddate><creator>Hegedus, Louis S</creator><creator>Geisler, Lisa</creator><creator>Riches, Andrew G</creator><creator>Salman, Sarri S</creator><creator>Umbricht, Gisela</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>20021101</creationdate><title>De Novo Synthesis of 4‘-Ethoxy Nucleoside Analogues</title><author>Hegedus, Louis S ; Geisler, Lisa ; Riches, Andrew G ; Salman, Sarri S ; Umbricht, Gisela</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-cadf8b78b557e1ab39b3af4308bc9f828728cf8bcc3988de9816a8c4f8045e7e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>4-Butyrolactone - analogs & derivatives</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Furans - chemistry</topic><topic>Hydroxylation</topic><topic>Molecular Structure</topic><topic>Nucleosides - chemical synthesis</topic><topic>Nucleosides - chemistry</topic><topic>Nucleosides, nucleotides and oligonucleotides</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hegedus, Louis S</creatorcontrib><creatorcontrib>Geisler, Lisa</creatorcontrib><creatorcontrib>Riches, Andrew G</creatorcontrib><creatorcontrib>Salman, Sarri S</creatorcontrib><creatorcontrib>Umbricht, Gisela</creatorcontrib><collection>Istex</collection><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 organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hegedus, Louis S</au><au>Geisler, Lisa</au><au>Riches, Andrew G</au><au>Salman, Sarri S</au><au>Umbricht, Gisela</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>De Novo Synthesis of 4‘-Ethoxy Nucleoside Analogues</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2002-11-01</date><risdate>2002</risdate><volume>67</volume><issue>22</issue><spage>7649</spage><epage>7655</epage><pages>7649-7655</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Butenolides 5a and 13 were used as optically active templates in the de novo synthesis of 4‘-disubstituted nucleoside analogues. The butenolides were reduced and acylated in situ to give acetates 10 and 14. Vorbrüggen coupling gave the protected nucleoside analogues 11 and 15. Reduction of 11 gave 4‘-ethoxy-2‘,3‘-dideoxythymidine (6) and deprotection of 15 gave 4‘-ethoxy-2‘,3‘-dideoxydidehydrothymidine (7). The cis-dihydroxylation of a variety of butenolides occurred with the major product formed from oxidation of the β-face.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12398485</pmid><doi>10.1021/jo020151f</doi><tpages>7</tpages></addata></record> |
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| subjects | 4-Butyrolactone - analogs & derivatives Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Furans - chemistry Hydroxylation Molecular Structure Nucleosides - chemical synthesis Nucleosides - chemistry Nucleosides, nucleotides and oligonucleotides Organic chemistry Preparations and properties Stereoisomerism |
| title | De Novo Synthesis of 4‘-Ethoxy Nucleoside Analogues |
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