Selective deuteration over raney nickel in deuterium oxide: Methyl glycosides
Identifieur interne : 001131 ( Istex/Corpus ); précédent : 001130; suivant : 001132Selective deuteration over raney nickel in deuterium oxide: Methyl glycosides
Auteurs : Stephen J. Angyal ; John D. Stevens ; Léon OdierSource :
- Carbohydrate Research [ 0008-6215 ] ; 1986.
English descriptors
- KwdEn :
- Angyal, Carbohydr, Carbon atom, Catalyst, Catalyst surface, Chem, Considerable exchange, Deuteration, Deuterium, Deuterium exchange, Deuterium oxide, Enol, Equatorial methoxyl group, Exchange reaction, Free hydroxyl group, Glycoside, Hydrogen atom, Hydrogen atoms, Hydroxyl, Hydroxyl group, Hydroxymethyl group, Koch, Lesser extent, Many instances, Methoxyl, Methoxyl group, Methyl, Methyl exchanges, Methyl glycosides, Nickel catalyst, Other positions, Pyranosides, Raney, Raney nickel, Reaction rates, Selecllve deuteration, Selective deuteration, Signals overlap, Similar rates, Small proportions, Such exchange, Various positions.
- Teeft :
- Angyal, Carbohydr, Carbon atom, Catalyst, Catalyst surface, Chem, Considerable exchange, Deuteration, Deuterium, Deuterium exchange, Deuterium oxide, Enol, Equatorial methoxyl group, Exchange reaction, Free hydroxyl group, Glycoside, Hydrogen atom, Hydrogen atoms, Hydroxyl, Hydroxyl group, Hydroxymethyl group, Koch, Lesser extent, Many instances, Methoxyl, Methoxyl group, Methyl, Methyl exchanges, Methyl glycosides, Nickel catalyst, Other positions, Pyranosides, Raney, Raney nickel, Reaction rates, Selecllve deuteration, Selective deuteration, Signals overlap, Similar rates, Small proportions, Such exchange, Various positions.
Abstract
Abstract: The rate of protium-deuterium exchange, catalyzed by deuterated Raney nickel in deuterium oxide, in various positions in methyl glycopyranosides and furanosides has been studied. In general, the exchange process is not highly regio-selective in these compounds. However, conditions were found under which methyl β-d-fructopyranoside can be selectively labelled on C-5, methyl β-d-fructofuranoside on C-3, and methyl β-d-galactopyranoside on C-3 and C-4.
Url:
DOI: 10.1016/0008-6215(86)85061-3
Links to Exploration step
ISTEX:5B29CE48BBA574728D1A30A4E70AAA8E41B3413ELe document en format XML
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In general, the exchange process is not highly regio-selective in these compounds. However, conditions were found under which methyl β-d-fructopyranoside can be selectively labelled on C-5, methyl β-d-fructofuranoside on C-3, and methyl β-d-galactopyranoside on C-3 and C-4.</div></front></TEI><istex><corpusName>elsevier</corpusName><keywords><teeft><json:string>deuterium</json:string><json:string>deuteration</json:string><json:string>methoxyl</json:string><json:string>glycoside</json:string><json:string>methyl</json:string><json:string>hydrogen atoms</json:string><json:string>methoxyl group</json:string><json:string>chem</json:string><json:string>hydroxyl</json:string><json:string>carbohydr</json:string><json:string>pyranosides</json:string><json:string>enol</json:string><json:string>raney</json:string><json:string>angyal</json:string><json:string>deuterium oxide</json:string><json:string>hydrogen atom</json:string><json:string>selective deuteration</json:string><json:string>methyl glycosides</json:string><json:string>catalyst surface</json:string><json:string>raney nickel</json:string><json:string>hydroxyl group</json:string><json:string>other positions</json:string><json:string>koch</json:string><json:string>hydroxymethyl group</json:string><json:string>many instances</json:string><json:string>methyl exchanges</json:string><json:string>deuterium exchange</json:string><json:string>catalyst</json:string><json:string>carbon atom</json:string><json:string>small proportions</json:string><json:string>free hydroxyl group</json:string><json:string>signals overlap</json:string><json:string>exchange reaction</json:string><json:string>reaction rates</json:string><json:string>similar rates</json:string><json:string>selecllve deuteration</json:string><json:string>such exchange</json:string><json:string>lesser extent</json:string><json:string>considerable exchange</json:string><json:string>nickel catalyst</json:string><json:string>various positions</json:string><json:string>equatorial methoxyl group</json:string></teeft></keywords><author><json:item><name>Stephen J. Angyal</name><affiliations><json:string>School of Chemistry, University of New South Wales, Kensington, N.S.W. 2033 Australia</json:string></affiliations></json:item><json:item><name>John D. Stevens</name><affiliations><json:string>School of Chemistry, University of New South Wales, Kensington, N.S.W. 2033 Australia</json:string></affiliations></json:item><json:item><name>Léon Odier</name><affiliations><json:string>Laboratoires de Chimie Départment de Recherche Fondamentale, Groupe Macromolécules Végétales, Centre d'Etudes Nucléaires de Grenoble, 85 X, F-38041 Grenoble France</json:string></affiliations></json:item></author><articleId><json:string>86850613</json:string></articleId><arkIstex>ark:/67375/6H6-QWJ61D21-G</arkIstex><language><json:string>eng</json:string></language><originalGenre><json:string>Full-length article</json:string></originalGenre><abstract>Abstract: The rate of protium-deuterium exchange, catalyzed by deuterated Raney nickel in deuterium oxide, in various positions in methyl glycopyranosides and furanosides has been studied. In general, the exchange process is not highly regio-selective in these compounds. However, conditions were found under which methyl β-d-fructopyranoside can be selectively labelled on C-5, methyl β-d-fructofuranoside on C-3, and methyl β-d-galactopyranoside on C-3 and C-4.</abstract><qualityIndicators><score>6.803</score><pdfWordCount>4059</pdfWordCount><pdfCharCount>24781</pdfCharCount><pdfVersion>1.2</pdfVersion><pdfPageCount>12</pdfPageCount><pdfPageSize>468 x 648 pts</pdfPageSize><refBibsNative>true</refBibsNative><abstractWordCount>62</abstractWordCount><abstractCharCount>463</abstractCharCount><keywordCount>0</keywordCount></qualityIndicators><title>Selective deuteration over raney nickel in deuterium oxide: Methyl glycosides</title><pii><json:string>0008-6215(86)85061-3</json:string></pii><genre><json:string>research-article</json:string></genre><host><title>Carbohydrate Research</title><language><json:string>unknown</json:string></language><publicationDate>1986</publicationDate><issn><json:string>0008-6215</json:string></issn><pii><json:string>S0008-6215(00)X0535-6</json:string></pii><volume>157</volume><pages><first>83</first><last>94</last></pages><genre><json:string>journal</json:string></genre></host><namedEntities><unitex><date><json:string>1986</json:string></date><geogName></geogName><orgName><json:string>University of New South Wales</json:string><json:string>Pierce Chemicals Co.</json:string></orgName><orgName_funder></orgName_funder><orgName_provider></orgName_provider><persName><json:string>E. 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For Part I, see ref. 1.</note></notesStmt><sourceDesc><biblStruct type="inbook"><analytic><title level="a" type="main" xml:lang="en">Selective deuteration over raney nickel in deuterium oxide: Methyl glycosides</title><author xml:id="author-0000"><persName><forename type="first">Stephen J.</forename><surname>Angyal</surname></persName><affiliation>School of Chemistry, University of New South Wales, Kensington, N.S.W. 2033 Australia</affiliation></author><author xml:id="author-0001"><persName><forename type="first">John D.</forename><surname>Stevens</surname></persName><affiliation>School of Chemistry, University of New South Wales, Kensington, N.S.W. 2033 Australia</affiliation></author><author xml:id="author-0002"><persName><forename type="first">Léon</forename><surname>Odier</surname></persName><note type="biography">On the staff of Université Scientifique et Médicale de Grenoble.</note><affiliation>On the staff of Université Scientifique et Médicale de Grenoble.</affiliation><affiliation>Laboratoires de Chimie Départment de Recherche Fondamentale, Groupe Macromolécules Végétales, Centre d'Etudes Nucléaires de Grenoble, 85 X, F-38041 Grenoble France</affiliation></author><idno type="istex">5B29CE48BBA574728D1A30A4E70AAA8E41B3413E</idno><idno type="DOI">10.1016/0008-6215(86)85061-3</idno><idno type="PII">0008-6215(86)85061-3</idno><idno type="ArticleID">86850613</idno></analytic><monogr><title level="j">Carbohydrate Research</title><title level="j" type="abbrev">CAR</title><idno type="pISSN">0008-6215</idno><idno type="PII">S0008-6215(00)X0535-6</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1986"></date><biblScope unit="volume">157</biblScope><biblScope unit="supplement">C</biblScope><biblScope unit="page" from="83">83</biblScope><biblScope unit="page" to="94">94</biblScope></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>1986</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>The rate of protium-deuterium exchange, catalyzed by deuterated Raney nickel in deuterium oxide, in various positions in methyl glycopyranosides and furanosides has been studied. In general, the exchange process is not highly regio-selective in these compounds. However, conditions were found under which methyl β-d-fructopyranoside can be selectively labelled on C-5, methyl β-d-fructofuranoside on C-3, and methyl β-d-galactopyranoside on C-3 and C-4.</p></abstract></profileDesc><revisionDesc><change when="1986">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/5B29CE48BBA574728D1A30A4E70AAA8E41B3413E/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Elsevier, elements deleted: tail"><istex:xmlDeclaration>version="1.0" encoding="UTF-8"</istex:xmlDeclaration><istex:docType PUBLIC="-//ES//DTD journal article DTD version 4.5.2//EN//XML" URI="art452.dtd" name="istex:docType"></istex:docType><istex:document><converted-article version="4.5.2" docsubtype="fla" xml:lang="en"><item-info><jid>CAR</jid><aid>86850613</aid><ce:pii>0008-6215(86)85061-3</ce:pii><ce:doi>10.1016/0008-6215(86)85061-3</ce:doi><ce:copyright type="unknown" year="1986"></ce:copyright></item-info><head><ce:article-footnote><ce:label>☆</ce:label><ce:note-para>Selective deuteration, Part II. For Part I, see ref. 1.</ce:note-para></ce:article-footnote><ce:title>Selective deuteration over raney nickel in deuterium oxide: Methyl glycosides</ce:title><ce:author-group><ce:author><ce:given-name>Stephen J.</ce:given-name><ce:surname>Angyal</ce:surname></ce:author><ce:author><ce:given-name>John D.</ce:given-name><ce:surname>Stevens</ce:surname></ce:author><ce:affiliation><ce:textfn>School of Chemistry, University of New South Wales, Kensington, N.S.W. 2033 Australia</ce:textfn></ce:affiliation></ce:author-group><ce:author-group><ce:author><ce:given-name>Léon</ce:given-name><ce:surname>Odier</ce:surname><ce:cross-ref refid="FN1"><ce:sup loc="post">1</ce:sup></ce:cross-ref></ce:author><ce:affiliation><ce:textfn>Laboratoires de Chimie Départment de Recherche Fondamentale, Groupe Macromolécules Végétales, Centre d'Etudes Nucléaires de Grenoble, 85 X, F-38041 Grenoble France</ce:textfn></ce:affiliation><ce:footnote id="FN1"><ce:label>1</ce:label><ce:note-para>On the staff of Université Scientifique et Médicale de Grenoble.</ce:note-para></ce:footnote></ce:author-group><ce:date-received day="20" month="3" year="1986"></ce:date-received><ce:date-accepted day="27" month="5" year="1986"></ce:date-accepted><ce:abstract class="author"><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para view="all" id="simple-para.0010">The rate of protium-deuterium exchange, catalyzed by deuterated Raney nickel in deuterium oxide, in various positions in methyl glycopyranosides and furanosides has been studied. In general, the exchange process is not highly regio-selective in these compounds. However, conditions were found under which methyl β-<ce:small-caps>d</ce:small-caps>-fructopyranoside can be selectively labelled on C-5, methyl β-<ce:small-caps>d</ce:small-caps>-fructofuranoside on C-3, and methyl β-<ce:small-caps>d</ce:small-caps>-galactopyranoside on C-3 and C-4.</ce:simple-para></ce:abstract-sec></ce:abstract></head></converted-article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Selective deuteration over raney nickel in deuterium oxide: Methyl glycosides</title></titleInfo><titleInfo type="alternative" lang="en" contentType="CDATA"><title>Selective deuteration over raney nickel in deuterium oxide: Methyl glycosides</title></titleInfo><name type="personal"><namePart type="given">Stephen J.</namePart><namePart type="family">Angyal</namePart><affiliation>School of Chemistry, University of New South Wales, Kensington, N.S.W. 2033 Australia</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">John D.</namePart><namePart type="family">Stevens</namePart><affiliation>School of Chemistry, University of New South Wales, Kensington, N.S.W. 2033 Australia</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Léon</namePart><namePart type="family">Odier</namePart><affiliation>Laboratoires de Chimie Départment de Recherche Fondamentale, Groupe Macromolécules Végétales, Centre d'Etudes Nucléaires de Grenoble, 85 X, F-38041 Grenoble France</affiliation><description>On the staff of Université Scientifique et Médicale de Grenoble.</description><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="Full-length article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-1JC4F85T-7">research-article</genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">1986</dateIssued><copyrightDate encoding="w3cdtf">1986</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><abstract lang="en">Abstract: The rate of protium-deuterium exchange, catalyzed by deuterated Raney nickel in deuterium oxide, in various positions in methyl glycopyranosides and furanosides has been studied. In general, the exchange process is not highly regio-selective in these compounds. However, conditions were found under which methyl β-d-fructopyranoside can be selectively labelled on C-5, methyl β-d-fructofuranoside on C-3, and methyl β-d-galactopyranoside on C-3 and C-4.</abstract><note>Selective deuteration, Part II. 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