A Novel Method for the Synthesis of Purine Nucleosides using Friedel-Crafts Catalysts

9-β-D-Ribofuranosyladenine was synthesized by condensation of N6-octanoyladenine (I) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (II) or 1, 2, 3, 5-tetra-O-acetyl-β-D-ribofuranose (III) in sym-dichloroethane or chlorobenzene in the presence of Friedel-Crafts catalysts followed by hydrolys...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1968/06/25, Vol.16(6), pp.1076-1080
Hauptverfasser:	FURUKAWA, YOSHIYASU, HONJO, MIKIO
Format:	Artikel
Sprache:	eng
Schlagworte:	Adenine Catalysis Methods Nucleosides - chemical synthesis Purines - chemical synthesis
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creator	FURUKAWA, YOSHIYASU HONJO, MIKIO
description	9-β-D-Ribofuranosyladenine was synthesized by condensation of N6-octanoyladenine (I) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (II) or 1, 2, 3, 5-tetra-O-acetyl-β-D-ribofuranose (III) in sym-dichloroethane or chlorobenzene in the presence of Friedel-Crafts catalysts followed by hydrolysis of the acyl groups. By this procedure the formation of the corresponding anomer was not observed Similarly, 9-β-D-ribopyranosyladenine was synthesized from I and 1, 2, 3, 4-tetra-O-acetyl-β-D-ribopyranose, and 9-β-D-ribofuranosylguanine in high yield from N2-palmitoylguanine and III.
doi_str_mv	10.1248/cpb.16.1076
format	Article
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By this procedure the formation of the corresponding anomer was not observed Similarly, 9-β-D-ribopyranosyladenine was synthesized from I and 1, 2, 3, 4-tetra-O-acetyl-β-D-ribopyranose, and 9-β-D-ribofuranosylguanine in high yield from N2-palmitoylguanine and III.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.16.1076</identifier><identifier>PMID: 5706815</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Adenine ; Catalysis ; Methods ; Nucleosides - chemical synthesis ; Purines - chemical synthesis</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1968/06/25, Vol.16(6), pp.1076-1080</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 1968</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c540t-ba53172267b5bcac1686f4e7288a44d2e0fc2450d6086c13b8c2cf6eca5cd7253</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/5706815$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>FURUKAWA, YOSHIYASU</creatorcontrib><creatorcontrib>HONJO, MIKIO</creatorcontrib><title>A Novel Method for the Synthesis of Purine Nucleosides using Friedel-Crafts Catalysts</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>9-β-D-Ribofuranosyladenine was synthesized by condensation of N6-octanoyladenine (I) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (II) or 1, 2, 3, 5-tetra-O-acetyl-β-D-ribofuranose (III) in sym-dichloroethane or chlorobenzene in the presence of Friedel-Crafts catalysts followed by hydrolysis of the acyl groups. By this procedure the formation of the corresponding anomer was not observed Similarly, 9-β-D-ribopyranosyladenine was synthesized from I and 1, 2, 3, 4-tetra-O-acetyl-β-D-ribopyranose, and 9-β-D-ribofuranosylguanine in high yield from N2-palmitoylguanine and III.</description><subject>Adenine</subject><subject>Catalysis</subject><subject>Methods</subject><subject>Nucleosides - chemical synthesis</subject><subject>Purines - chemical synthesis</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1968</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkM2LEzEYh4Moa3f15FkICF6WqflOelyqq8K6CrrnkMm8s50yndS8GaH_vSktK3jJe_g9PISHkDecLblQ7kPct0tulpxZ84wsuFS20ULI52TBGFs1Qhr5klwibhkTmll5QS60ZcZxvSAPN_Q-_YGRfoOySR3tU6ZlA_TnYaoHB6Sppz_mPExA7-c4QsKhA6QzDtMjvc0DdDA26xz6gnQdShgPWPAVedGHEeH1-V6Rh9tPv9Zfmrvvn7-ub-6aqBUrTRu05FYIY1vdxhC5caZXYIVzQalOAOujUJp1hjkTuWxdFLE3EIOOnRVaXpH3J-8-p98zYPG7ASOMY5ggzeidZivFnajgu__AbZrzVP_mudIryxUXtlLXJyrmhJih9_s87EI-eM78MbWvqT03_pi60m_PzrndQffEntvW_eNp32IJj_C0h1yGGvLo4ivtjj5zfqr237wJ2cMk_wKouJCk</recordid><startdate>19680101</startdate><enddate>19680101</enddate><creator>FURUKAWA, YOSHIYASU</creator><creator>HONJO, MIKIO</creator><general>The Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>19680101</creationdate><title>A Novel Method for the Synthesis of Purine Nucleosides using Friedel-Crafts Catalysts</title><author>FURUKAWA, YOSHIYASU ; HONJO, MIKIO</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c540t-ba53172267b5bcac1686f4e7288a44d2e0fc2450d6086c13b8c2cf6eca5cd7253</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1968</creationdate><topic>Adenine</topic><topic>Catalysis</topic><topic>Methods</topic><topic>Nucleosides - chemical synthesis</topic><topic>Purines - chemical synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>FURUKAWA, YOSHIYASU</creatorcontrib><creatorcontrib>HONJO, MIKIO</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>FURUKAWA, YOSHIYASU</au><au>HONJO, MIKIO</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Novel Method for the Synthesis of Purine Nucleosides using Friedel-Crafts Catalysts</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1968-01-01</date><risdate>1968</risdate><volume>16</volume><issue>6</issue><spage>1076</spage><epage>1080</epage><pages>1076-1080</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>9-β-D-Ribofuranosyladenine was synthesized by condensation of N6-octanoyladenine (I) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (II) or 1, 2, 3, 5-tetra-O-acetyl-β-D-ribofuranose (III) in sym-dichloroethane or chlorobenzene in the presence of Friedel-Crafts catalysts followed by hydrolysis of the acyl groups. By this procedure the formation of the corresponding anomer was not observed Similarly, 9-β-D-ribopyranosyladenine was synthesized from I and 1, 2, 3, 4-tetra-O-acetyl-β-D-ribopyranose, and 9-β-D-ribofuranosylguanine in high yield from N2-palmitoylguanine and III.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>5706815</pmid><doi>10.1248/cpb.16.1076</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record>
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subjects	Adenine Catalysis Methods Nucleosides - chemical synthesis Purines - chemical synthesis
title	A Novel Method for the Synthesis of Purine Nucleosides using Friedel-Crafts Catalysts
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