Synthesis of 4-substituted 2-aminopyrrolo[2,3-d]pyrimidine 2′,3′-dideoxyribonucleosides
A number of new 2‐aminopyrrolo[2,3‐d]pyrimidine N‐7‐(2′,3′‐dideoxyribonucleosides) (11–13 and 15) were synthesized. These are related to 7‐deaza‐2′,3′‐dideoxyguanosine (14), but carry various substituents at C‐4. 2‐Amino‐4‐chloro‐7‐(2′,3′‐dideoxy‐β‐D‐glycero‐pentofuranosyl)‐7H‐pyrrolo[2,3‐d]‐pyrimid...
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| Veröffentlicht in: | Liebigs Annalen der Chemie 1990-03, Vol.1990 (3), p.227-232 |
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| container_title | Liebigs Annalen der Chemie |
| container_volume | 1990 |
| creator | Seela, Frank Muth, Heinz-Peter |
| description | A number of new 2‐aminopyrrolo[2,3‐d]pyrimidine N‐7‐(2′,3′‐dideoxyribonucleosides) (11–13 and 15) were synthesized. These are related to 7‐deaza‐2′,3′‐dideoxyguanosine (14), but carry various substituents at C‐4. 2‐Amino‐4‐chloro‐7‐(2′,3′‐dideoxy‐β‐D‐glycero‐pentofuranosyl)‐7H‐pyrrolo[2,3‐d]‐pyrimidine (3) was used as a common intermediate, and was obtained from the corresponding 2′‐deoxyribonucleoside 4 by selective silylation of 5′‐OH and Barton deoxygenation of 3′‐OH. |
| doi_str_mv | 10.1002/jlac.199019900141 |
| format | Article |
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These are related to 7‐deaza‐2′,3′‐dideoxyguanosine (14), but carry various substituents at C‐4. 2‐Amino‐4‐chloro‐7‐(2′,3′‐dideoxy‐β‐D‐glycero‐pentofuranosyl)‐7H‐pyrrolo[2,3‐d]‐pyrimidine (3) was used as a common intermediate, and was obtained from the corresponding 2′‐deoxyribonucleoside 4 by selective silylation of 5′‐OH and Barton deoxygenation of 3′‐OH.</description><identifier>ISSN: 0170-2041</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/jlac.199019900141</identifier><identifier>CODEN: LACHDL</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>2′,3′‐Dideoxyribonucleosides ; 3-d]pyrimidines ; 3′-Dideoxyribonucleosides ; Barton deoxygenation ; Carbohydrates. Nucleosides and nucleotides ; Chemistry ; Exact sciences and technology ; HIV ; HIV, potential agent against ; Nucleosides, nucleotides and oligonucleotides ; Organic chemistry ; potential agent against ; Preparations and properties ; Pyrrolo ; Pyrrolo[2,3‐d]pyrimidines</subject><ispartof>Liebigs Annalen der Chemie, 1990-03, Vol.1990 (3), p.227-232</ispartof><rights>Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>1990 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3681-1d32ed0f6a74902b3d6d6b059387d21a0a584fd5beb879e3b289dcc84dd6dda3</citedby><cites>FETCH-LOGICAL-c3681-1d32ed0f6a74902b3d6d6b059387d21a0a584fd5beb879e3b289dcc84dd6dda3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjlac.199019900141$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjlac.199019900141$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=6801691$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Seela, Frank</creatorcontrib><creatorcontrib>Muth, Heinz-Peter</creatorcontrib><title>Synthesis of 4-substituted 2-aminopyrrolo[2,3-d]pyrimidine 2′,3′-dideoxyribonucleosides</title><title>Liebigs Annalen der Chemie</title><addtitle>Liebigs Ann. Chem</addtitle><description>A number of new 2‐aminopyrrolo[2,3‐d]pyrimidine N‐7‐(2′,3′‐dideoxyribonucleosides) (11–13 and 15) were synthesized. These are related to 7‐deaza‐2′,3′‐dideoxyguanosine (14), but carry various substituents at C‐4. 2‐Amino‐4‐chloro‐7‐(2′,3′‐dideoxy‐β‐D‐glycero‐pentofuranosyl)‐7H‐pyrrolo[2,3‐d]‐pyrimidine (3) was used as a common intermediate, and was obtained from the corresponding 2′‐deoxyribonucleoside 4 by selective silylation of 5′‐OH and Barton deoxygenation of 3′‐OH.</description><subject>2′,3′‐Dideoxyribonucleosides</subject><subject>3-d]pyrimidines</subject><subject>3′-Dideoxyribonucleosides</subject><subject>Barton deoxygenation</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>HIV</subject><subject>HIV, potential agent against</subject><subject>Nucleosides, nucleotides and oligonucleotides</subject><subject>Organic chemistry</subject><subject>potential agent against</subject><subject>Preparations and properties</subject><subject>Pyrrolo</subject><subject>Pyrrolo[2,3‐d]pyrimidines</subject><issn>0170-2041</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1990</creationdate><recordtype>article</recordtype><recordid>eNqFUE1LAzEQDaJgrf4Abz14bOok2a-cpBRt1UXBFjwUCdlNFlO3m7LZYvfmb_In-UvcZaWIFw8zw8y892Z4CJ0TGBEAernKZToinEMbQDxygHoEOMcQcDhEPSAhYAoeOUYnzq0API_4tIeW87qoXrUzbmCzgYfdNnGVqbaVVgOK5doUdlOXpc3tkg4ZVi9NZ9ZGmUIP6NfH55A1CSujtN01m8QW2zTX1jUDd4qOMpk7ffZT-2hxc72YzHD8OL2djGOcsiAimChGtYIskKHHgSZMBSpIwOcsChUlEqQfeZnyE51EIdcsoRFXaRp5qgEqyfqIdLJpaZ0rdSY2zYuyrAUB0ZojWnPEb3MazkXH2UiXyjwrZZEatycGEZCAt7CrDvZucl3_ryvu4vHkzyHcKRhX6d1eQZZvIghZ6Ivnh6nwYf40i--ZIOwbfSSJgw</recordid><startdate>19900312</startdate><enddate>19900312</enddate><creator>Seela, Frank</creator><creator>Muth, Heinz-Peter</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19900312</creationdate><title>Synthesis of 4-substituted 2-aminopyrrolo[2,3-d]pyrimidine 2′,3′-dideoxyribonucleosides</title><author>Seela, Frank ; Muth, Heinz-Peter</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3681-1d32ed0f6a74902b3d6d6b059387d21a0a584fd5beb879e3b289dcc84dd6dda3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1990</creationdate><topic>2′,3′‐Dideoxyribonucleosides</topic><topic>3-d]pyrimidines</topic><topic>3′-Dideoxyribonucleosides</topic><topic>Barton deoxygenation</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>HIV</topic><topic>HIV, potential agent against</topic><topic>Nucleosides, nucleotides and oligonucleotides</topic><topic>Organic chemistry</topic><topic>potential agent against</topic><topic>Preparations and properties</topic><topic>Pyrrolo</topic><topic>Pyrrolo[2,3‐d]pyrimidines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Seela, Frank</creatorcontrib><creatorcontrib>Muth, Heinz-Peter</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Liebigs Annalen der Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Seela, Frank</au><au>Muth, Heinz-Peter</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 4-substituted 2-aminopyrrolo[2,3-d]pyrimidine 2′,3′-dideoxyribonucleosides</atitle><jtitle>Liebigs Annalen der Chemie</jtitle><addtitle>Liebigs Ann. Chem</addtitle><date>1990-03-12</date><risdate>1990</risdate><volume>1990</volume><issue>3</issue><spage>227</spage><epage>232</epage><pages>227-232</pages><issn>0170-2041</issn><eissn>1099-0690</eissn><coden>LACHDL</coden><abstract>A number of new 2‐aminopyrrolo[2,3‐d]pyrimidine N‐7‐(2′,3′‐dideoxyribonucleosides) (11–13 and 15) were synthesized. These are related to 7‐deaza‐2′,3′‐dideoxyguanosine (14), but carry various substituents at C‐4. 2‐Amino‐4‐chloro‐7‐(2′,3′‐dideoxy‐β‐D‐glycero‐pentofuranosyl)‐7H‐pyrrolo[2,3‐d]‐pyrimidine (3) was used as a common intermediate, and was obtained from the corresponding 2′‐deoxyribonucleoside 4 by selective silylation of 5′‐OH and Barton deoxygenation of 3′‐OH.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/jlac.199019900141</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0170-2041 |
| ispartof | Liebigs Annalen der Chemie, 1990-03, Vol.1990 (3), p.227-232 |
| issn | 0170-2041 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_jlac_199019900141 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | 2′,3′‐Dideoxyribonucleosides 3-d]pyrimidines 3′-Dideoxyribonucleosides Barton deoxygenation Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology HIV HIV, potential agent against Nucleosides, nucleotides and oligonucleotides Organic chemistry potential agent against Preparations and properties Pyrrolo Pyrrolo[2,3‐d]pyrimidines |
| title | Synthesis of 4-substituted 2-aminopyrrolo[2,3-d]pyrimidine 2′,3′-dideoxyribonucleosides |
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