Synthesis of methyl 3-amino-3,6-dideoxy-alpha-d-galactopyranoside carrying different amide substituents
2013 (English)In: RSC Advances, ISSN 2046-2069, Vol. 3, no 45, 23090-23097 p.Article in journal (Refereed) Published
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.
IdentifiersURN: urn:nbn:se:su:diva-97407DOI: 10.1039/c3ra45092aISI: 000326395800056OAI: oai:DiVA.org:su-97407DiVA: diva2:678019
FunderSwedish Research CouncilKnut and Alice Wallenberg Foundation