Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals
•Synthesis of exo-glycals by the Wittig reaction of glycosyl phosphonium salts.•Effective and selective hydrogenation using Pd/C(en)catalyst.•Optimization of experimental conditions.•Synthesis of novel 2-deoxy-β-benzyl-C-glycosides. Novel 2-deoxy-β-benzyl-C-glycosides were prepared in good yields an...
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| Veröffentlicht in: | Carbohydrate research 2014-07, Vol.393, p.23-25 |
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| container_title | Carbohydrate research |
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| creator | Díaz, Gisela Ponzinibbio, Agustín Bravo, Rodolfo Daniel |
| description | •Synthesis of exo-glycals by the Wittig reaction of glycosyl phosphonium salts.•Effective and selective hydrogenation using Pd/C(en)catalyst.•Optimization of experimental conditions.•Synthesis of novel 2-deoxy-β-benzyl-C-glycosides.
Novel 2-deoxy-β-benzyl-C-glycosides were prepared in good yields and excellent stereoselectivity by a route involving the Wittig reaction of glycosyl phosphonium salts and reduction of exo-glycals as key steps. Hydrogenation of benzyl protected enol ethers was performed with Pd/C(en) as an effective chemoselective catalyst to afford exclusively β anomers. |
| doi_str_mv | 10.1016/j.carres.2014.04.009 |
| format | Article |
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Novel 2-deoxy-β-benzyl-C-glycosides were prepared in good yields and excellent stereoselectivity by a route involving the Wittig reaction of glycosyl phosphonium salts and reduction of exo-glycals as key steps. Hydrogenation of benzyl protected enol ethers was performed with Pd/C(en) as an effective chemoselective catalyst to afford exclusively β anomers.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/j.carres.2014.04.009</identifier><identifier>PMID: 24887703</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>C-Glycosides ; exo-Glycals ; Glycosides - chemical synthesis ; Glycosides - chemistry ; Hydrogenation ; Molecular Conformation ; Palladium catalyst ; Stereoisomerism ; Wittig reaction</subject><ispartof>Carbohydrate research, 2014-07, Vol.393, p.23-25</ispartof><rights>2014 Elsevier Ltd</rights><rights>Copyright © 2014 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c408t-230d50acb99f01523e5c4fa096316cc1085031de0f43a2e6f26e6c5262b62c193</citedby><cites>FETCH-LOGICAL-c408t-230d50acb99f01523e5c4fa096316cc1085031de0f43a2e6f26e6c5262b62c193</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S000862151400161X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24887703$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Díaz, Gisela</creatorcontrib><creatorcontrib>Ponzinibbio, Agustín</creatorcontrib><creatorcontrib>Bravo, Rodolfo Daniel</creatorcontrib><title>Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>•Synthesis of exo-glycals by the Wittig reaction of glycosyl phosphonium salts.•Effective and selective hydrogenation using Pd/C(en)catalyst.•Optimization of experimental conditions.•Synthesis of novel 2-deoxy-β-benzyl-C-glycosides.
Novel 2-deoxy-β-benzyl-C-glycosides were prepared in good yields and excellent stereoselectivity by a route involving the Wittig reaction of glycosyl phosphonium salts and reduction of exo-glycals as key steps. Hydrogenation of benzyl protected enol ethers was performed with Pd/C(en) as an effective chemoselective catalyst to afford exclusively β anomers.</description><subject>C-Glycosides</subject><subject>exo-Glycals</subject><subject>Glycosides - chemical synthesis</subject><subject>Glycosides - chemistry</subject><subject>Hydrogenation</subject><subject>Molecular Conformation</subject><subject>Palladium catalyst</subject><subject>Stereoisomerism</subject><subject>Wittig reaction</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMGKFDEQhoMo7rj6BiI5eslYSbrT3RdBBncVFjysgreQTqqnM_R01lTPsO1j-SD7TPY4q0eh4Kfgr_-nPsZeS1hLkObdbu1dzkhrBbJYwzLQPGErWVdaFMp8f8pWAFALo2R5wV4Q7ZYVTGWeswtV1HVVgV4xup3HqUeKxFPHx3TEgSsRMN3P4uGXaHH8OQ9iI7bD7BPFgMTbmfdx2w8zpwkzJsHdGLjvcZ8IB_RTPCLv55DTFkc3xTSeovE-_QlxA71kz7pF8NWjXrJvVx-_bj6Jmy_XnzcfboQvoJ6E0hBKcL5tmg5kqTSWvugcNEZL472EugQtA0JXaKfQdMqg8aUyqjXKy0Zfsrfn3LucfhyQJruP5HEY3IjpQFaW2pi6qJRarMXZ6nMiytjZuxz3Ls9Wgj3htjt7xm1PuC0sA6eGN48Nh3aP4d_RX76L4f3ZgMufx4jZko84egwxL6RsSPH_Db8BjSOUoQ</recordid><startdate>20140701</startdate><enddate>20140701</enddate><creator>Díaz, Gisela</creator><creator>Ponzinibbio, Agustín</creator><creator>Bravo, Rodolfo Daniel</creator><general>Elsevier Ltd</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>7X8</scope></search><sort><creationdate>20140701</creationdate><title>Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals</title><author>Díaz, Gisela ; Ponzinibbio, Agustín ; Bravo, Rodolfo Daniel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c408t-230d50acb99f01523e5c4fa096316cc1085031de0f43a2e6f26e6c5262b62c193</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>C-Glycosides</topic><topic>exo-Glycals</topic><topic>Glycosides - chemical synthesis</topic><topic>Glycosides - chemistry</topic><topic>Hydrogenation</topic><topic>Molecular Conformation</topic><topic>Palladium catalyst</topic><topic>Stereoisomerism</topic><topic>Wittig reaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Díaz, Gisela</creatorcontrib><creatorcontrib>Ponzinibbio, Agustín</creatorcontrib><creatorcontrib>Bravo, Rodolfo Daniel</creatorcontrib><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>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Díaz, Gisela</au><au>Ponzinibbio, Agustín</au><au>Bravo, Rodolfo Daniel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2014-07-01</date><risdate>2014</risdate><volume>393</volume><spage>23</spage><epage>25</epage><pages>23-25</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>•Synthesis of exo-glycals by the Wittig reaction of glycosyl phosphonium salts.•Effective and selective hydrogenation using Pd/C(en)catalyst.•Optimization of experimental conditions.•Synthesis of novel 2-deoxy-β-benzyl-C-glycosides.
Novel 2-deoxy-β-benzyl-C-glycosides were prepared in good yields and excellent stereoselectivity by a route involving the Wittig reaction of glycosyl phosphonium salts and reduction of exo-glycals as key steps. Hydrogenation of benzyl protected enol ethers was performed with Pd/C(en) as an effective chemoselective catalyst to afford exclusively β anomers.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>24887703</pmid><doi>10.1016/j.carres.2014.04.009</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Carbohydrate research, 2014-07, Vol.393, p.23-25 |
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| language | eng |
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| subjects | C-Glycosides exo-Glycals Glycosides - chemical synthesis Glycosides - chemistry Hydrogenation Molecular Conformation Palladium catalyst Stereoisomerism Wittig reaction |
| title | Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals |
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