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Synthesis of methyl 3-amino-3,6-dideoxy-alpha-d-galactopyranoside carrying different amide substituents
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2013 (English)In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 3, no 45, 23090-23097 p.Article in journal (Refereed) Published
Abstract [en]

Bacterial polysaccharides may contain rare sugars of different stereochemistry and diverse functional groups; the repertoire can be further extended by varying the exocyclic substituents. Synthesis of four monosaccharides is described utilizing a suitably protected key intermediate obtained by regioselective acetal ring-opening reduction, dexoygenation at C6, alcohol oxidation at C3 followed by formation of an oxime, which was stereoselectively reduced by samarium diiodide to give a 3-amino-derivative having the desired galacto-configuration. Subsequent functionalization was performed resulting in one to four carbon atoms in the amide substituent.

Place, publisher, year, edition, pages
2013. Vol. 3, no 45, 23090-23097 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-97407DOI: 10.1039/c3ra45092aISI: 000326395800056OAI: oai:DiVA.org:su-97407DiVA: diva2:678019
Funder
Swedish Research CouncilKnut and Alice Wallenberg Foundation
Note

AuthorCount:3;

Available from: 2013-12-11 Created: 2013-12-09 Last updated: 2017-12-06Bibliographically approved

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Mobarak, HaniEngström, OlofWidmalm, Göran
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