Towards the synthesis of the disaccharide fragment of pradimicin

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dc.contributor Aalto-yliopisto fi
dc.contributor Aalto University en Maunula, Tatja 2012-02-13T12:43:57Z 2012-02-13T12:43:57Z 2004-06-18
dc.identifier.isbn 951-22-7038-2
dc.identifier.issn 1457-6295
dc.description.abstract Pradimicin is a novel antibiotic consisting of a benzo[a]naphthacenequinone aglycon, an amino acid and a disaccharide fragment. In this study, the α-analogue of the disaccharide derivative of pradimicin A was synthesized in its protected form. The disaccharide moiety of pradimicin A was built up from a suitably protected, commercially available D-xylose derivative and the amino sugar part, synthesized from L-threonine. The synthesis of the target amino sugar started with the conversion of the L-threonine derived aldehyde to the desired E-enoate via a modified Horner-Wadsworth-Emmons olefination. Ruthenium-catalyzed cis-dihydroxylation of the double bond produced a mixture of anti- and syn-aminodiols, of which the former was lactonized under acidic conditions. Platinum-catalyzed reduction of the lactone produced a mixture of lactols, which upon treatment with DAST provided a mixture of α- and β-fluorinated amino sugar derivatives. Both the α- and β-fluorides were transformed to suitable glycosyl fluorides of pradimicin A via successive N-methylation by MeI/Ag2O, deacetylation and regioselective benzoyl protection at the C2-position. Final coupling of the α-glycosyl fluoride with the D-xylose derived thioglycoside donor by NBS furnished the protected α-analogue of the disaccharide fragment of pradimicin A. en
dc.format.extent 145
dc.format.mimetype application/pdf
dc.language.iso en en
dc.publisher Helsinki University of Technology en
dc.publisher Teknillinen korkeakoulu fi
dc.relation.ispartofseries Report / Helsinki University of Technology, Department of Chemistry, Laboratory of Organic Chemistry en
dc.relation.ispartofseries 1/2004 en
dc.subject.other Chemistry en
dc.title Towards the synthesis of the disaccharide fragment of pradimicin en
dc.type G4 Monografiaväitöskirja fi
dc.description.version reviewed en
dc.contributor.department Department of Chemical Technology en
dc.contributor.department Kemian tekniikan osasto fi
dc.subject.keyword amino sugars en
dc.subject.keyword antibiotics en
dc.subject.keyword antifungal en
dc.subject.keyword asymmetric synthesis en
dc.subject.keyword glycosyl fluoride en
dc.identifier.urn urn:nbn:fi:tkk-003561
dc.type.dcmitype text en
dc.type.ontasot Väitöskirja (monografia) fi
dc.type.ontasot Doctoral dissertation (monograph) en
dc.contributor.lab Laboratory of Organic Chemistry en
dc.contributor.lab Orgaanisen kemian laboratorio fi

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