Synthesis of the Phosphoramidite Derivative of 2‘-Deoxy-2‘-C-β-methylcytidine
2‘-Deoxy-2‘-C-β-methylnucleosides elicit interest as potential therapeutic agents and as analogues for the analysis of nucleic acid structure and function. An efficient route for the synthesis of 2‘-deoxy-2‘-C-methyluridine (11), 2‘-deoxy-2‘-C-methylcytidine (12), and the phosphoramidite derivative...
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| Veröffentlicht in: | Journal of organic chemistry 2003-08, Vol.68 (17), p.6799-6802 |
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| container_end_page | 6802 |
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| container_issue | 17 |
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| container_title | Journal of organic chemistry |
| container_volume | 68 |
| creator | Li, Nan-Sheng Piccirilli, Joseph A |
| description | 2‘-Deoxy-2‘-C-β-methylnucleosides elicit interest as potential therapeutic agents and as analogues for the analysis of nucleic acid structure and function. An efficient route for the synthesis of 2‘-deoxy-2‘-C-methyluridine (11), 2‘-deoxy-2‘-C-methylcytidine (12), and the phosphoramidite derivative of 2‘-deoxy-2‘-C-β-methylcytidine (10, 46% overall yield) from 1,2,3,5-tetra-O-benzoyl-2-C-β-methylribofuranose (1) is described. |
| doi_str_mv | 10.1021/jo034263y |
| format | Article |
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An efficient route for the synthesis of 2‘-deoxy-2‘-C-methyluridine (11), 2‘-deoxy-2‘-C-methylcytidine (12), and the phosphoramidite derivative of 2‘-deoxy-2‘-C-β-methylcytidine (10, 46% overall yield) from 1,2,3,5-tetra-O-benzoyl-2-C-β-methylribofuranose (1) is described.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo034263y</identifier><identifier>PMID: 12919052</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Cytidine - analogs & derivatives ; Deoxycytidine - analogs & derivatives ; Deoxycytidine - chemical synthesis ; Deoxycytidine - chemistry ; Indicators and Reagents ; Magnetic Resonance Spectroscopy ; Models, Molecular ; Uridine - analogs & derivatives</subject><ispartof>Journal of organic chemistry, 2003-08, Vol.68 (17), p.6799-6802</ispartof><rights>Copyright © 2003 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a349t-3baae0d25cae0b2c0628bcde48bf11203e50c15fd291e0f66052969f181e31eb3</citedby><cites>FETCH-LOGICAL-a349t-3baae0d25cae0b2c0628bcde48bf11203e50c15fd291e0f66052969f181e31eb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo034263y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo034263y$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12919052$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Nan-Sheng</creatorcontrib><creatorcontrib>Piccirilli, Joseph A</creatorcontrib><title>Synthesis of the Phosphoramidite Derivative of 2‘-Deoxy-2‘-C-β-methylcytidine</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>2‘-Deoxy-2‘-C-β-methylnucleosides elicit interest as potential therapeutic agents and as analogues for the analysis of nucleic acid structure and function. An efficient route for the synthesis of 2‘-deoxy-2‘-C-methyluridine (11), 2‘-deoxy-2‘-C-methylcytidine (12), and the phosphoramidite derivative of 2‘-deoxy-2‘-C-β-methylcytidine (10, 46% overall yield) from 1,2,3,5-tetra-O-benzoyl-2-C-β-methylribofuranose (1) is described.</description><subject>Cytidine - analogs & derivatives</subject><subject>Deoxycytidine - analogs & derivatives</subject><subject>Deoxycytidine - chemical synthesis</subject><subject>Deoxycytidine - chemistry</subject><subject>Indicators and Reagents</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Models, Molecular</subject><subject>Uridine - analogs & derivatives</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM9OwkAQxjdGI4gefAHTiyYeVvdPt7RHA4oaEomgHjfb7TQUW4q7hdCbj-Fz-CA-hE_iIgQvzmUmmd_MN_MhdEzJBSWMXk5Kwn0W8HoHNalgBAcR8XdRkxDGMHeNBjqwdkJcCCH2UYOyiEZEsCZ6HNbTagw2s16Zeq7yBuPSzsalUUWWZBV4XTDZQlXZAlYE-37_wF0olzX-LTv46xMXUI3rXNeVm5jCIdpLVW7haJNb6OnmetS5xf2H3l3nqo8V96MK81gpIAkT2qWYaRKwMNYJ-GGcUsoIB0E0FWnibgWSBoG7NwqilIYUOIWYt9DZeu_MlG9zsJUsMqshz9UUyrmVbe6e5aHvwPM1qE1prYFUzkxWKFNLSuTKQLk10LEnm6XzuIDkj9w45gC8BjJbwXLbV-ZVBm3eFnI0GMre6IU9D8KBvHf86ZpX2jqduZk6T_4R_gHitIjX</recordid><startdate>20030822</startdate><enddate>20030822</enddate><creator>Li, Nan-Sheng</creator><creator>Piccirilli, Joseph A</creator><general>American Chemical Society</general><scope>BSCLL</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>20030822</creationdate><title>Synthesis of the Phosphoramidite Derivative of 2‘-Deoxy-2‘-C-β-methylcytidine</title><author>Li, Nan-Sheng ; Piccirilli, Joseph A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a349t-3baae0d25cae0b2c0628bcde48bf11203e50c15fd291e0f66052969f181e31eb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Cytidine - analogs & derivatives</topic><topic>Deoxycytidine - analogs & derivatives</topic><topic>Deoxycytidine - chemical synthesis</topic><topic>Deoxycytidine - chemistry</topic><topic>Indicators and Reagents</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Models, Molecular</topic><topic>Uridine - analogs & derivatives</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Nan-Sheng</creatorcontrib><creatorcontrib>Piccirilli, Joseph A</creatorcontrib><collection>Istex</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>Li, Nan-Sheng</au><au>Piccirilli, Joseph A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of the Phosphoramidite Derivative of 2‘-Deoxy-2‘-C-β-methylcytidine</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-08-22</date><risdate>2003</risdate><volume>68</volume><issue>17</issue><spage>6799</spage><epage>6802</epage><pages>6799-6802</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>2‘-Deoxy-2‘-C-β-methylnucleosides elicit interest as potential therapeutic agents and as analogues for the analysis of nucleic acid structure and function. An efficient route for the synthesis of 2‘-deoxy-2‘-C-methyluridine (11), 2‘-deoxy-2‘-C-methylcytidine (12), and the phosphoramidite derivative of 2‘-deoxy-2‘-C-β-methylcytidine (10, 46% overall yield) from 1,2,3,5-tetra-O-benzoyl-2-C-β-methylribofuranose (1) is described.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>12919052</pmid><doi>10.1021/jo034263y</doi><tpages>4</tpages></addata></record> |
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| language | eng |
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| source | American Chemical Society; MEDLINE |
| subjects | Cytidine - analogs & derivatives Deoxycytidine - analogs & derivatives Deoxycytidine - chemical synthesis Deoxycytidine - chemistry Indicators and Reagents Magnetic Resonance Spectroscopy Models, Molecular Uridine - analogs & derivatives |
| title | Synthesis of the Phosphoramidite Derivative of 2‘-Deoxy-2‘-C-β-methylcytidine |
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