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.
Descripteurs français
- Pascal (Inist)
English descriptors
- KwdEn :
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.
Affiliations:
Links toward previous steps (curation, corpus...)
- to stream PascalFrancis, to step Corpus: 001A81
- to stream PascalFrancis, to step Curation: 004463
- to stream PascalFrancis, to step Checkpoint: 001633
- to stream Main, to step Merge: 006A84
- to stream Main, to step Curation: 006683
Le document en format XML
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<series><title level="j" type="main">Journal of organic chemistry</title>
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<term>Configuration retention</term>
<term>Glycomimetic compound</term>
<term>Glycoside</term>
<term>Oside</term>
<term>Protecting group</term>
<term>Stereochemistry</term>
<term>Sulfonamide</term>
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<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>
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<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>
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<tree><country name="Australie"><noRegion><name sortKey="Lopez, Marie" sort="Lopez, Marie" uniqKey="Lopez M" first="Marie" last="Lopez">Marie Lopez</name>
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<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>
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