About: Glycosidic juvenogens: Derivatives bearing alpha,beta-unsaturated ester functionalities     Goto   Sponge   NotDistinct   Permalink

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Description
  • Byla připravena skupina chráněných alkyl glykosidů, odvozených od mateřských isomerních alkoholů (bioanalogů hmyzích juvenilních hormonů; juvenoidů) v racemických a v enantiomerně čistých formách. Uhličitan kademnatý byl použit jako promotor Koenigs-Knorrovy reakce. Odstranění chránících skupin bylo provedeno ethanolýzou za přítomnosti octanu zinečnatého. Připravené juvenogeny (racemické i enantiomerně čisté sloučeniny) byly podrobeny detailní analýze pomocí 1H a 13C NMR spektroskopie a rovněž základnímu biologickému testování na plošticích Pyrrhocoris apterus. (cs)
  • A series of the protected alkyl glycosides 5a/5b-12a/12b was synthesized from the parent isomeric alcohols (insect juvenile hormone bioanalogs; juvenoids), 4-[4'-(2%22-hydroxycyclohexyl)methylphenoxy]-3-methyl-but-2-enoic acid ethyl ester (Ia/1b-4a/4b; racemic structures) and (1a-4a; enantiopure structures). Cadmium carbonate was used as a promoter of this Koenigs-Knorr reaction. and the products were obtained in 82 92% yields. Deprotection of the carbohydrate functionality of 5a/5b-12a/12b was carefully, performed using ethanolysis in the presence of zinc acetate, due to the presence of another ester functionality in the aglycone part of the molecule of protected alkyl glycosides. Resulting alkyl glycosides 13a/13b-20a/20b (diastereoisomeric mixtures) and 13a20a (enantiopure compounds), biochemically activated hormonogenic compounds juvenogens), were obtained in 82-93/() yields. Finally, chiral HPLC separation of the diastereoisoineric mixtures of alkyl glycosides was applied to get sufficient quant...
  • A series of the protected alkyl glycosides 5a/5b-12a/12b was synthesized from the parent isomeric alcohols (insect juvenile hormone bioanalogs; juvenoids), 4-[4'-(2%22-hydroxycyclohexyl)methylphenoxy]-3-methyl-but-2-enoic acid ethyl ester (Ia/1b-4a/4b; racemic structures) and (1a-4a; enantiopure structures). Cadmium carbonate was used as a promoter of this Koenigs-Knorr reaction. and the products were obtained in 82 92% yields. Deprotection of the carbohydrate functionality of 5a/5b-12a/12b was carefully, performed using ethanolysis in the presence of zinc acetate, due to the presence of another ester functionality in the aglycone part of the molecule of protected alkyl glycosides. Resulting alkyl glycosides 13a/13b-20a/20b (diastereoisomeric mixtures) and 13a20a (enantiopure compounds), biochemically activated hormonogenic compounds juvenogens), were obtained in 82-93/() yields. Finally, chiral HPLC separation of the diastereoisoineric mixtures of alkyl glycosides was applied to get sufficient quant... (en)
Title
  • Glycosidic juvenogens: Derivatives bearing alpha,beta-unsaturated ester functionalities
  • Glykosidické juvenogeny: Deriváty nesoucí alfa,beta-nenasycené esterové funkce (cs)
  • Glycosidic juvenogens: Derivatives bearing alpha,beta-unsaturated ester functionalities (en)
skos:prefLabel
  • Glycosidic juvenogens: Derivatives bearing alpha,beta-unsaturated ester functionalities
  • Glykosidické juvenogeny: Deriváty nesoucí alfa,beta-nenasycené esterové funkce (cs)
  • Glycosidic juvenogens: Derivatives bearing alpha,beta-unsaturated ester functionalities (en)
skos:notation
  • RIV/61388963:_____/07:00090755!RIV08-AV0-61388963
http://linked.open.../vavai/riv/strany
  • 7126;7137
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • P(OC D29.001), V, Z(AV0Z40550506), Z(AV0Z50380511)
http://linked.open...iv/cisloPeriodika
  • 22
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 423502
http://linked.open...ai/riv/idVysledku
  • RIV/61388963:_____/07:00090755
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • Pyrrhocoris apterus; juvenogen; insect juvenile hormone analog (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV
  • [783E66B60502]
http://linked.open...i/riv/nazevZdroje
  • Bioorganic & Medicinal Chemistry
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 15
http://linked.open...iv/tvurceVysledku
  • Jedlička, Pavel
  • Wimmer, Zdeněk
  • Šaman, David
  • Kolehmainen, E.
  • Wimmerová, Martina
  • Pechová, L.
  • Sile, L.
http://linked.open...n/vavai/riv/zamer
issn
  • 0968-0896
number of pages
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