Synthesis of Sulfonamide-Bridged Glycomimetics
Identifieur interne : 006683 ( Main/Exploration ); précédent : 006682; suivant : 006684Synthesis of Sulfonamide-Bridged Glycomimetics
Auteurs : Marie Lopez [Australie] ; Laurent F. Bornaghi [Australie] ; Hugues Driguez [France] ; Sally-Ann Poulsen [Australie]Source :
- Journal of organic chemistry [ 0022-3263 ] ; 2011.
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- Pascal (Inist)
English descriptors
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Abstract
A flexible and short synthesis of sulfonamide-bridged di-, tri-, tetra-, and octasaccharide glycomimetics was accomplished by reaction of glycosyl thioacetates with amino sugar substrates. The chemistry to incorporate the sulfonamide linker in place of a native O-glycosidic bond was broadly scoped, allowing access to head-to-head (1↔1) and head-to-tail (1→2), (1→3), (1→4), and (1→6) sulfonamide-bridged glycomimetics. The synthesis proceeds with retention of configuration at the anomeric center and is compatible with variable stereochemical arrangements and with acid- and base-labile protecting groups.
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Bornaghi</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Eskitis Institute, Griffith University, Nathan Campus</s1><s2>Queensland, 4111</s2><s3>AUS</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>4 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>Queensland, 4111</wicri:noRegion></affiliation></author><author><name sortKey="Driguez, Hugues" sort="Driguez, Hugues" uniqKey="Driguez H" first="Hugues" last="Driguez">Hugues Driguez</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Centre de Recherche sur les Macromolécules Végétales, UPR-CNRS 5301, BP53</s1><s2>38041 Grenoble</s2><s3>FRA</s3><sZ>3 aut.</sZ></inist:fA14><country>France</country><wicri:noRegion>38041 Grenoble</wicri:noRegion><placeName><settlement type="city">Grenoble</settlement><region type="region" nuts="2">Auvergne-Rhône-Alpes</region><region type="old region" nuts="2">Rhône-Alpes</region></placeName></affiliation></author><author><name sortKey="Poulsen, Sally Ann" sort="Poulsen, Sally Ann" uniqKey="Poulsen S" first="Sally-Ann" last="Poulsen">Sally-Ann Poulsen</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Eskitis Institute, Griffith University, Nathan Campus</s1><s2>Queensland, 4111</s2><s3>AUS</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>4 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>Queensland, 4111</wicri:noRegion></affiliation></author></analytic><series><title level="j" type="main">Journal of organic chemistry</title><title level="j" type="abbreviated">J. org. chem.</title><idno type="ISSN">0022-3263</idno><imprint><date when="2011">2011</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Journal of organic chemistry</title><title level="j" type="abbreviated">J. org. chem.</title><idno type="ISSN">0022-3263</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aminosugar</term><term>Anomer</term><term>Chemical synthesis</term><term>Configuration retention</term><term>Glycomimetic compound</term><term>Glycoside</term><term>Oside</term><term>Protecting group</term><term>Stereochemistry</term><term>Sulfonamide</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Synthèse chimique</term><term>Sulfonamide</term><term>Glycoside</term><term>Ose amine</term><term>Rétention configuration</term><term>Anomère</term><term>Stéréochimie</term><term>Groupe protecteur</term><term>Oside</term><term>Thioacétique acide dérivé</term><term>Composé glycomimétique</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A flexible and short synthesis of sulfonamide-bridged di-, tri-, tetra-, and octasaccharide glycomimetics was accomplished by reaction of glycosyl thioacetates with amino sugar substrates. The chemistry to incorporate the sulfonamide linker in place of a native O-glycosidic bond was broadly scoped, allowing access to head-to-head (1↔1) and head-to-tail (1→2), (1→3), (1→4), and (1→6) sulfonamide-bridged glycomimetics. The synthesis proceeds with retention of configuration at the anomeric center and is compatible with variable stereochemical arrangements and with acid- and base-labile protecting groups.</div></front></TEI><affiliations><list><country><li>Australie</li><li>France</li></country><region><li>Auvergne-Rhône-Alpes</li><li>Rhône-Alpes</li></region><settlement><li>Grenoble</li></settlement></list><tree><country name="Australie"><noRegion><name sortKey="Lopez, Marie" sort="Lopez, Marie" uniqKey="Lopez M" first="Marie" last="Lopez">Marie Lopez</name></noRegion><name sortKey="Bornaghi, Laurent F" sort="Bornaghi, Laurent F" uniqKey="Bornaghi L" first="Laurent F." last="Bornaghi">Laurent F. Bornaghi</name><name sortKey="Poulsen, Sally Ann" sort="Poulsen, Sally Ann" uniqKey="Poulsen S" first="Sally-Ann" last="Poulsen">Sally-Ann Poulsen</name></country><country name="France"><region name="Auvergne-Rhône-Alpes"><name sortKey="Driguez, Hugues" sort="Driguez, Hugues" uniqKey="Driguez H" first="Hugues" last="Driguez">Hugues Driguez</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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