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

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	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 w 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 w (en)
Title	Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones (en)
skos:prefLabel	Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones (en)
skos:notation	RIV/70883521:28110/10:63509363!RIV11-GA0-28110___
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(GA203/07/0320), P(MEB090603), Z(MSM7088352101)
http://linked.open...iv/cisloPeriodika	6
http://linked.open...vai/riv/dodaniDat	2011
http://linked.open...aciTvurceVysledku	Kimmel, Roman Kafka, Stanislav
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Tomáše Bati ve Zlíně / Fakulta technologická
http://linked.open...dnocenehoVysledku	286800
http://linked.open...ai/riv/idVysledku	RIV/70883521:28110/10:63509363
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	4-Hydroxyquinolin-2(1H)-ones; Glycosylation; Koenigs?Knorr method; Deacetylation; NMR structure elucidation. (en)
http://linked.open.../riv/klicoveSlovo	Glycosylation 4-Hydroxyquinolin-2(1H)-ones Deacetylation Koenigs?Knorr method NMR structure elucidation.
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[B7B15B3C017F]
http://linked.open...i/riv/nazevZdroje	Carbohydrate Research
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	2 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...vavai/riv/projekt	New transformations of quinolinediones Transformations of 3-hydroxy, 3-amino, and 3-thiocyanatoquinoline-2,4(1H,3H)-diones to novel heterocyclic systems
http://linked.open...UplatneniVysledku	2010
http://linked.open...v/svazekPeriodika	345
http://linked.open...iv/tvurceVysledku	Kafka, Stanislav Košmrlj, J. Kimmel, Roman
http://linked.open...n/vavai/riv/zamer	Multifunctional Composite Systems Based on Natural and Synthetic Polymers
issn	0008-6215
number of pages	11 (xsd:int)
http://localhost/t...ganizacniJednotka	28110
is http://linked.open...avai/riv/vysledek of	Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

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