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Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

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dc.title Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones en
dc.contributor.author Kimmel, Roman
dc.contributor.author Kafka, Stanislav
dc.contributor.author Košmrlj, Janez
dc.relation.ispartof Carbohydrate Research
dc.identifier.issn 0008-6215 OCLC, Ulrich, Sherpa/RoMEO, JCR
dc.date.issued 2010
utb.relation.volume 345
utb.relation.issue 6
dc.citation.spage 768
dc.citation.epage 779
dc.type article
dc.language.iso en
dc.publisher Elsevier Science, Ltd. en
dc.identifier.doi 10.1016/j.carres.2010.01.023
dc.relation.uri https://www.sciencedirect.com/science/article/pii/S0008621510000479
dc.subject 4-Hydroxyquinolin-2(1H)-ones en
dc.subject Glycosylation en
dc.subject Koenigs?Knorr method en
dc.subject Deacetylation en
dc.subject NMR structure elucidation. en
dc.description.abstract Byla popsána selektivní glukosylace N-nesubstituovaných 4-hydroxychinolin-2-(1H)-onů na 4-(tetra-O-acetyl-?-D-glukopyranosyloxy)chinolin-2(1H)-ony. Byly testovány čtyři glykosylové donory zahrnující tetra-O-acetyl-?-D-glukopyranosylbromid, pentaacetát ?-D-glukosy, tetraacetát glukosy a tetra-O-acetyl-?-D-glukopyranosyl-trichloracetimidát s různými promotory a reakčními podmínkami. Nejlepší výsledky byly získány s tetra-O-acetyl-?-D-glukopyranosylbromidem s Cs2CO3 v CH3CN. V některých případech byla 4 O glukosylace chinolinonového kruhu doprovázena 2-O-glukosylací poskytující odpovídající 2,4 bis(2,3,4,6-tetra-O-acetyl-?-D-glukopyranosyloxy)?chinolin jako vedlejší produkt. Následně byly 4-(tetra-O-acetyl-?-D-glukopyranosyloxy)chinolin-2(1H)-ony působením triethylaminu v methanolu deacetylovány na 4-(?-D-glukopyranosyloxy)chinolin-2(1H)-ony. V některých případech byla deacetylace doprovázena štěpením glykosidové vazby. Objasnění struktury, kompletní přiřazení protonových a uhlíkových jaderných rezonancí, stejně jako určení anomerní konfigurace u všech studovaných produktů, bylo provedeno pomocí 1D a 2D NMR spektroskopie. cs
dc.description.abstract A comparative study for selective glucosylation of N-unsubstituted 4 hydroxyquinolin-2(1H)-ones into 4-(tetra-O-acetyl-?-D-glucopyranosyloxy)quinolin-2(1H)-ones is reported. Four glycosyl donors including tetra-O-acetyl-?-D-glucopyranosyl bromide, ?-D-glucose pentaacetate, glucose tetraacetate and tetra-O-acetyl-?-D-glucopyranosyl trichloroacetimidate were tested, along with different promoters and reaction conditions. The best results were obtained with tetra-O-acetyl-?-D-glucopyranosyl bromide with Cs2CO3 in CH3CN. In some cases the 4-O-glucosylation of the quinolinone ring was accompanied by 2-O-glucosylation yielding the corresponding 2,4-bis(tetra-O-acetyl-?-D-glucopyranosyloxy)quinoline. Next, 4-(tetra-O-acetyl-?-D-glucopyranosyloxy)quinolin-2(1H)-ones were deacetylated into 4-(?-D-glucopyranosyloxy)quinolin-2(1H)-ones with Et3N in MeOH. In some instances the deacetylation was accompanied by the sugar?aglycone bond cleavage. Structure elucidation, complete assignment of proton and carbon resonances as well as assignment of anomeric configuration for all the products under investigation were performed by 1D and 2D NMR spectroscopy. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1001141
utb.identifier.rivid RIV/70883521:28110/10:63509363!RIV11-GA0-28110___
utb.identifier.obdid 43864063
utb.identifier.scopus 2-s2.0-77949567772
utb.identifier.wok 000277112800006
utb.source j-riv
utb.contributor.internalauthor Kimmel, Roman
utb.contributor.internalauthor Kafka, Stanislav
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