Synthesis of two mono-deoxy β-cyclodextrin derivatives as useful tools for confirming DIBAL-H promoted bis-de-O-methylation mechanism
Diisobutylaluminium hydride （DIBAL-H） promotes secondary rim regioselective bis-de-O-methylation of permethylated β- cyclodextrin （β-CD） to give diol 2. To gain an insight into the mechanism of this remarkable regioselective behavior, two corresponding permethylated β-CDs with an alcohol function at...
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| Veröffentlicht in: | Chinese chemical letters 2012-12, Vol.23 (12), p.1315-1318 |
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| creator | Xiao, Su Long Zhou, De Min Yang, Ming Yu, Fei Zhang, Li He Sinaÿ, Pierre Zhang, Yong Min |
| description | Diisobutylaluminium hydride （DIBAL-H） promotes secondary rim regioselective bis-de-O-methylation of permethylated β- cyclodextrin （β-CD） to give diol 2. To gain an insight into the mechanism of this remarkable regioselective behavior, two corresponding permethylated β-CDs with an alcohol function at either 2- or 3-position were synthesized in our previous study. As a step further to this work, the two compounds were subjected to deoxygenation reaction with tributyltin hydride in the present of 2,2＇- azobisisobutyronitrile affording the corresponding 2- and 3-deoxy permethylated β-CD derivatives （19 and 16）. The structures of these two compounds were characterized by 1D and 2D NMR and HRMS. Compounds 16 and 19 were unable to react with DIBAL- H which suggests that O-2A and O-3B are necessary for DIBAL-H promoted bis-de-O-methylation reaction of permethylated β-CD. |
| doi_str_mv | 10.1016/j.cclet.2012.10.023 |
| format | Article |
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To gain an insight into the mechanism of this remarkable regioselective behavior, two corresponding permethylated β-CDs with an alcohol function at either 2- or 3-position were synthesized in our previous study. As a step further to this work, the two compounds were subjected to deoxygenation reaction with tributyltin hydride in the present of 2,2＇- azobisisobutyronitrile affording the corresponding 2- and 3-deoxy permethylated β-CD derivatives （19 and 16）. The structures of these two compounds were characterized by 1D and 2D NMR and HRMS. Compounds 16 and 19 were unable to react with DIBAL- H which suggests that O-2A and O-3B are necessary for DIBAL-H promoted bis-de-O-methylation reaction of permethylated β-CD.</description><identifier>ISSN: 1001-8417</identifier><identifier>EISSN: 1878-5964</identifier><identifier>DOI: 10.1016/j.cclet.2012.10.023</identifier><language>eng</language><publisher>Elsevier B.V</publisher><subject>Cyclodextrin (CD) ; Deoxy ; DIBAL-H ; Mechanism ; Synthesis ; 偶氮二异丁腈 ; 区域选择性 ; 合成 ; 工具 ; 机制 ; 环糊精衍生物 ; 甲基化反应 ; 脱氧反应</subject><ispartof>Chinese chemical letters, 2012-12, Vol.23 (12), p.1315-1318</ispartof><rights>2012 Yong Min Zhang</rights><rights>Copyright © Wanfang Data Co. Ltd. All Rights Reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c361t-1be27c5aae991d85eed4b71e16f6e37e5ac0004f6356f2f568385e1447b1c9353</citedby><cites>FETCH-LOGICAL-c361t-1be27c5aae991d85eed4b71e16f6e37e5ac0004f6356f2f568385e1447b1c9353</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Uhttp://image.cqvip.com/vip1000/qk/84039X/84039X.jpg</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S1001841712003567$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids></links><search><creatorcontrib>Xiao, Su Long</creatorcontrib><creatorcontrib>Zhou, De Min</creatorcontrib><creatorcontrib>Yang, Ming</creatorcontrib><creatorcontrib>Yu, Fei</creatorcontrib><creatorcontrib>Zhang, Li He</creatorcontrib><creatorcontrib>Sinaÿ, Pierre</creatorcontrib><creatorcontrib>Zhang, Yong Min</creatorcontrib><title>Synthesis of two mono-deoxy β-cyclodextrin derivatives as useful tools for confirming DIBAL-H promoted bis-de-O-methylation mechanism</title><title>Chinese chemical letters</title><addtitle>Chinese Chemical Letters</addtitle><description>Diisobutylaluminium hydride （DIBAL-H） promotes secondary rim regioselective bis-de-O-methylation of permethylated β- cyclodextrin （β-CD） to give diol 2. To gain an insight into the mechanism of this remarkable regioselective behavior, two corresponding permethylated β-CDs with an alcohol function at either 2- or 3-position were synthesized in our previous study. As a step further to this work, the two compounds were subjected to deoxygenation reaction with tributyltin hydride in the present of 2,2＇- azobisisobutyronitrile affording the corresponding 2- and 3-deoxy permethylated β-CD derivatives （19 and 16）. The structures of these two compounds were characterized by 1D and 2D NMR and HRMS. Compounds 16 and 19 were unable to react with DIBAL- H which suggests that O-2A and O-3B are necessary for DIBAL-H promoted bis-de-O-methylation reaction of permethylated β-CD.</description><subject>Cyclodextrin (CD)</subject><subject>Deoxy</subject><subject>DIBAL-H</subject><subject>Mechanism</subject><subject>Synthesis</subject><subject>偶氮二异丁腈</subject><subject>区域选择性</subject><subject>合成</subject><subject>工具</subject><subject>机制</subject><subject>环糊精衍生物</subject><subject>甲基化反应</subject><subject>脱氧反应</subject><issn>1001-8417</issn><issn>1878-5964</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkM1u1DAQxyMEEqXwBFzMiZMXO3ac7IEDtEArVeoBOFuOM954STzF9m43PAAPxIPwTHjZiiunGY3-H5pfVb3kbMUZV2-2K2snyKua8bpcVqwWj6oz3rUdbdZKPi47Y5x2krdPq2cpbRmru06os-rn5yXkEZJPBB3J90hmDEgHwMNCfv-idrETDnDI0QcyQPR7k_0eEjGJ7BK43UQy4pSIw0gsBufj7MOGXF6_f3dDr8hdxBkzDKT3qaTSWzpDHpeppGAgM9jRBJ_m59UTZ6YELx7mefX144cvF1f05vbT9UVJskLxTHkPdWsbY2C95kPXAAyybzlw5RSIFhpjGWPSKdEoV7tGdaKIuJRtz-1aNOK8en3KvTfBmbDRW9zFUBr1j814-NYfAfK6sCpKcVLaiClFcPou-tnERXOmj9D1Vv-Fro-e47FAL663JxeUJ_Yeok7WQ7Aw-Ag26wH9f_yvHlpHDJvvheS_Willp8pz4g-1WJm8</recordid><startdate>20121201</startdate><enddate>20121201</enddate><creator>Xiao, Su Long</creator><creator>Zhou, De Min</creator><creator>Yang, Ming</creator><creator>Yu, Fei</creator><creator>Zhang, Li He</creator><creator>Sinaÿ, Pierre</creator><creator>Zhang, Yong Min</creator><general>Elsevier B.V</general><general>Institut Parisien de Chimie Molécutaire, UMR CNRS 7201, Université Pierre et Marie Curie-Paris 6, 4 Place Jussieu, 75005 Paris, France%State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China%Institut Parisien de Chimie Molécutaire, UMR CNRS 7201, Université Pierre et Marie Curie-Paris 6, 4 Place Jussieu, 75005 Paris, France%Institut Parisien de Chimie Molécutaire, UMR CNRS 7201, Université Pierre et Marie Curie-Paris 6, 4 Place Jussieu, 75005 Paris, France</general><general>Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, China</general><general>State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China</general><scope>2RA</scope><scope>92L</scope><scope>CQIGP</scope><scope>~WA</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>2B.</scope><scope>4A8</scope><scope>92I</scope><scope>93N</scope><scope>PSX</scope><scope>TCJ</scope></search><sort><creationdate>20121201</creationdate><title>Synthesis of two mono-deoxy β-cyclodextrin derivatives as useful tools for confirming DIBAL-H promoted bis-de-O-methylation mechanism</title><author>Xiao, Su Long ; Zhou, De Min ; Yang, Ming ; Yu, Fei ; Zhang, Li He ; Sinaÿ, Pierre ; Zhang, Yong Min</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c361t-1be27c5aae991d85eed4b71e16f6e37e5ac0004f6356f2f568385e1447b1c9353</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Cyclodextrin (CD)</topic><topic>Deoxy</topic><topic>DIBAL-H</topic><topic>Mechanism</topic><topic>Synthesis</topic><topic>偶氮二异丁腈</topic><topic>区域选择性</topic><topic>合成</topic><topic>工具</topic><topic>机制</topic><topic>环糊精衍生物</topic><topic>甲基化反应</topic><topic>脱氧反应</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xiao, Su Long</creatorcontrib><creatorcontrib>Zhou, De Min</creatorcontrib><creatorcontrib>Yang, Ming</creatorcontrib><creatorcontrib>Yu, Fei</creatorcontrib><creatorcontrib>Zhang, Li He</creatorcontrib><creatorcontrib>Sinaÿ, Pierre</creatorcontrib><creatorcontrib>Zhang, Yong Min</creatorcontrib><collection>中文科技期刊数据库</collection><collection>中文科技期刊数据库-CALIS站点</collection><collection>中文科技期刊数据库-7.0平台</collection><collection>中文科技期刊数据库- 镜像站点</collection><collection>CrossRef</collection><collection>Wanfang Data Journals - Hong Kong</collection><collection>WANFANG Data Centre</collection><collection>Wanfang Data Journals</collection><collection>万方数据期刊 - 香港版</collection><collection>China Online Journals (COJ)</collection><collection>China Online Journals (COJ)</collection><jtitle>Chinese chemical letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xiao, Su Long</au><au>Zhou, De Min</au><au>Yang, Ming</au><au>Yu, Fei</au><au>Zhang, Li He</au><au>Sinaÿ, Pierre</au><au>Zhang, Yong Min</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of two mono-deoxy β-cyclodextrin derivatives as useful tools for confirming DIBAL-H promoted bis-de-O-methylation mechanism</atitle><jtitle>Chinese chemical letters</jtitle><addtitle>Chinese Chemical Letters</addtitle><date>2012-12-01</date><risdate>2012</risdate><volume>23</volume><issue>12</issue><spage>1315</spage><epage>1318</epage><pages>1315-1318</pages><issn>1001-8417</issn><eissn>1878-5964</eissn><abstract>Diisobutylaluminium hydride （DIBAL-H） promotes secondary rim regioselective bis-de-O-methylation of permethylated β- cyclodextrin （β-CD） to give diol 2. To gain an insight into the mechanism of this remarkable regioselective behavior, two corresponding permethylated β-CDs with an alcohol function at either 2- or 3-position were synthesized in our previous study. As a step further to this work, the two compounds were subjected to deoxygenation reaction with tributyltin hydride in the present of 2,2＇- azobisisobutyronitrile affording the corresponding 2- and 3-deoxy permethylated β-CD derivatives （19 and 16）. The structures of these two compounds were characterized by 1D and 2D NMR and HRMS. Compounds 16 and 19 were unable to react with DIBAL- H which suggests that O-2A and O-3B are necessary for DIBAL-H promoted bis-de-O-methylation reaction of permethylated β-CD.</abstract><pub>Elsevier B.V</pub><doi>10.1016/j.cclet.2012.10.023</doi><tpages>4</tpages></addata></record> |
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| ispartof | Chinese chemical letters, 2012-12, Vol.23 (12), p.1315-1318 |
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| subjects | Cyclodextrin (CD) Deoxy DIBAL-H Mechanism Synthesis 偶氮二异丁腈 区域选择性 合成 工具 机制 环糊精衍生物 甲基化反应 脱氧反应 |
| title | Synthesis of two mono-deoxy β-cyclodextrin derivatives as useful tools for confirming DIBAL-H promoted bis-de-O-methylation mechanism |
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