Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties
The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-...
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| Veröffentlicht in: | Carbohydrate research 2015-01, Vol.402, p.25-34 |
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| creator | Redpath, Philip Ness, Kerry A. Rousseau, Joanne Macdonald, Simon J.F. Migaud, Marie E. |
| description | The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series, we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (±)-β-2-deoxy-glucose 6-phosphate. [Display omitted]
•Access to a range of (±) C-glycosides shows the versatility of the tandem ene/IMSC.•Diastereomerically pure C-glycosides incorporating aromatic moieties were prepared.•The C-homologue of (±)-β-2-deoxy-glucose 6-phosphate is also reported.
The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series, we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (±)-β-2-deoxy-glucose 6-phosphate. [Display omitted] |
| doi_str_mv | 10.1016/j.carres.2014.10.030 |
| format | Article |
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•Access to a range of (±) C-glycosides shows the versatility of the tandem ene/IMSC.•Diastereomerically pure C-glycosides incorporating aromatic moieties were prepared.•The C-homologue of (±)-β-2-deoxy-glucose 6-phosphate is also reported.
The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series, we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (±)-β-2-deoxy-glucose 6-phosphate. [Display omitted]</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/j.carres.2014.10.030</identifier><identifier>PMID: 25486220</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Benzoic Acid - chemistry ; C-Glycoside ; C-Nucleoside ; Glucose-6-Phosphate - analogs & derivatives ; Glucose-6-Phosphate - chemistry ; Glucose-6-phosphate bioisostere ; Monosaccharides - chemistry ; Stereoisomerism ; Tandem ene/intramolecular Sakurai cyclisation ; Transmetallation</subject><ispartof>Carbohydrate research, 2015-01, Vol.402, p.25-34</ispartof><rights>2014 Elsevier Ltd</rights><rights>Copyright © 2014 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-cc38de2ce4b3fad4496eb9af8afb36a6d233b9aa91c9f66941698ab15b75f3533</citedby><cites>FETCH-LOGICAL-c362t-cc38de2ce4b3fad4496eb9af8afb36a6d233b9aa91c9f66941698ab15b75f3533</cites><orcidid>0000-0003-0255-1298</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.carres.2014.10.030$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25486220$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Redpath, Philip</creatorcontrib><creatorcontrib>Ness, Kerry A.</creatorcontrib><creatorcontrib>Rousseau, Joanne</creatorcontrib><creatorcontrib>Macdonald, Simon J.F.</creatorcontrib><creatorcontrib>Migaud, Marie E.</creatorcontrib><title>Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series, we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (±)-β-2-deoxy-glucose 6-phosphate. [Display omitted]
•Access to a range of (±) C-glycosides shows the versatility of the tandem ene/IMSC.•Diastereomerically pure C-glycosides incorporating aromatic moieties were prepared.•The C-homologue of (±)-β-2-deoxy-glucose 6-phosphate is also reported.
The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series, we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (±)-β-2-deoxy-glucose 6-phosphate. [Display omitted]</description><subject>Benzoic Acid - chemistry</subject><subject>C-Glycoside</subject><subject>C-Nucleoside</subject><subject>Glucose-6-Phosphate - analogs & derivatives</subject><subject>Glucose-6-Phosphate - chemistry</subject><subject>Glucose-6-phosphate bioisostere</subject><subject>Monosaccharides - chemistry</subject><subject>Stereoisomerism</subject><subject>Tandem ene/intramolecular Sakurai cyclisation</subject><subject>Transmetallation</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE-LFDEQxYMo7rj6DURy9NJj_nWmcxFkcFVY8KLgLaQrlSVDd2dM9Sj77TfDrOLJU1GvXtWjfoy9lmIrhbTvDlsItSJtlZCmSVuhxRO2kcNOd0bZH0_ZRggxdFbJ_oq9IDq0Vtidfc6uVG8Gq5TYsMNNgDwhDwBIxNfCF_zN993ddA-FckTiYYn_CpwgpFSmSDwvUOqx1LDm5Y6n0wJrLkuYMmHkoZa5DYDPJeOakV6yZylMhK8e6zX7fvPx2_5zd_v105f9h9sOtFVrB6CHiArQjDqFaIyzOLqQhpBGbYONSuvWByfBJWudkdYNYZT9uOuT7rW-Zm8vd4-1_DwhrX7OBDhNYcFyIi-tkdI55VyzmosVaiGqmPyx5jnUey-FP1P2B3-h7M-Uz2qj3NbePCacxhnj36U_WJvh_cWA7c9fGasnyLgAxlwRVh9L_n_CAyK8kjI</recordid><startdate>20150130</startdate><enddate>20150130</enddate><creator>Redpath, Philip</creator><creator>Ness, Kerry A.</creator><creator>Rousseau, Joanne</creator><creator>Macdonald, Simon J.F.</creator><creator>Migaud, Marie E.</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><orcidid>https://orcid.org/0000-0003-0255-1298</orcidid></search><sort><creationdate>20150130</creationdate><title>Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties</title><author>Redpath, Philip ; Ness, Kerry A. ; Rousseau, Joanne ; Macdonald, Simon J.F. ; Migaud, Marie E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-cc38de2ce4b3fad4496eb9af8afb36a6d233b9aa91c9f66941698ab15b75f3533</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Benzoic Acid - chemistry</topic><topic>C-Glycoside</topic><topic>C-Nucleoside</topic><topic>Glucose-6-Phosphate - analogs & derivatives</topic><topic>Glucose-6-Phosphate - chemistry</topic><topic>Glucose-6-phosphate bioisostere</topic><topic>Monosaccharides - chemistry</topic><topic>Stereoisomerism</topic><topic>Tandem ene/intramolecular Sakurai cyclisation</topic><topic>Transmetallation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Redpath, Philip</creatorcontrib><creatorcontrib>Ness, Kerry A.</creatorcontrib><creatorcontrib>Rousseau, Joanne</creatorcontrib><creatorcontrib>Macdonald, Simon J.F.</creatorcontrib><creatorcontrib>Migaud, Marie E.</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>Redpath, Philip</au><au>Ness, Kerry A.</au><au>Rousseau, Joanne</au><au>Macdonald, Simon J.F.</au><au>Migaud, Marie E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2015-01-30</date><risdate>2015</risdate><volume>402</volume><spage>25</spage><epage>34</epage><pages>25-34</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series, we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (±)-β-2-deoxy-glucose 6-phosphate. [Display omitted]
•Access to a range of (±) C-glycosides shows the versatility of the tandem ene/IMSC.•Diastereomerically pure C-glycosides incorporating aromatic moieties were prepared.•The C-homologue of (±)-β-2-deoxy-glucose 6-phosphate is also reported.
The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series, we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (±)-β-2-deoxy-glucose 6-phosphate. [Display omitted]</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>25486220</pmid><doi>10.1016/j.carres.2014.10.030</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-0255-1298</orcidid></addata></record> |
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| subjects | Benzoic Acid - chemistry C-Glycoside C-Nucleoside Glucose-6-Phosphate - analogs & derivatives Glucose-6-Phosphate - chemistry Glucose-6-phosphate bioisostere Monosaccharides - chemistry Stereoisomerism Tandem ene/intramolecular Sakurai cyclisation Transmetallation |
| title | Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties |
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