About: Modular synthesis of 5-substituted thiophen-2-yl C-2'-deoxyribonucleosides     Goto   Sponge   NotDistinct   Permalink

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  • A new modular methodology for the preparation of 5-substituted thiophen-2-yl C-nucleosides was developed. A Friedel–Crafts-type of C-glycosidation of 2-bromothiophene with bis-toluoyl protected methylglycoside gave the desired bis-toluoyl protected 1-beta-(5-bromothiophen-2-yl)-1,2-dideoxyribofuranose in 60%. Deprotection of the protected product gave free bromothiophene C-nucleoside, which was reprotected to bis-TBDMS protected C-nucleoside. The key intermediates were then subjected to a series of palladium catalyzed cross-coupling reactions to afford, after suitable deprotection, a series of free C-nucleosides. Alternatively, other types of C-nucleosides were prepared directly by aqueous-phase Suzuki cross-coupling reactions of free C-nucleosides with boronic acids.
  • A new modular methodology for the preparation of 5-substituted thiophen-2-yl C-nucleosides was developed. A Friedel–Crafts-type of C-glycosidation of 2-bromothiophene with bis-toluoyl protected methylglycoside gave the desired bis-toluoyl protected 1-beta-(5-bromothiophen-2-yl)-1,2-dideoxyribofuranose in 60%. Deprotection of the protected product gave free bromothiophene C-nucleoside, which was reprotected to bis-TBDMS protected C-nucleoside. The key intermediates were then subjected to a series of palladium catalyzed cross-coupling reactions to afford, after suitable deprotection, a series of free C-nucleosides. Alternatively, other types of C-nucleosides were prepared directly by aqueous-phase Suzuki cross-coupling reactions of free C-nucleosides with boronic acids. (en)
  • Byla vyvinuta nová modulární metodika pro přípravu 5-substituovaných thiofen-2-yl C-nukleosidů. Friedel-Craftsův typ C-glykosidace 2-bromothiofenu s bis-toluoyl chráněným methylglykosidem poskytla požadovaný 1-beta-(5-bromthiofen-2-yl)-1,2-dideoxyribofuranosid v 60% výtěžku. Odchránění toluoylovaného produktu poskytlo volný bromthiofen C-nukleosid, který byl následně ochráněn pomocí TBDMS chránicí skupiny za vzniku bis-TBDMS chráněného C-nukleosidu. Klíčové chráněné C-nukleosidy byly poté využity pro palladiem katalyzované cross-coupling reakce. Následné vhodné odchránění produktů cross-coupling reakcí poskytlo sérií volných aryl a alkyl C-nukleosidů. Dále byla vyzkoušena přímá příprava volných C-nukleosidů pomocí Suzuki cross-coupling reakcí ve vodné fázi, za použití boronových kyselin a volného bromthiofen C-nukleosidu. (cs)
Title
  • Modular synthesis of 5-substituted thiophen-2-yl C-2'-deoxyribonucleosides
  • Modular synthesis of 5-substituted thiophen-2-yl C-2'-deoxyribonucleosides (en)
  • Modulární syntéza 5-substituovaných thiofen-2-yl C-2'-deoxyribonukleosidů (cs)
skos:prefLabel
  • Modular synthesis of 5-substituted thiophen-2-yl C-2'-deoxyribonucleosides
  • Modular synthesis of 5-substituted thiophen-2-yl C-2'-deoxyribonucleosides (en)
  • Modulární syntéza 5-substituovaných thiofen-2-yl C-2'-deoxyribonukleosidů (cs)
skos:notation
  • RIV/61388963:_____/08:00309912!RIV09-AV0-61388963
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • P(LC512), Z(AV0Z40550506)
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
  • 380266
http://linked.open...ai/riv/idVysledku
  • RIV/61388963:_____/08:00309912
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • modular methodology; C-nucleosides; 5-bromothiophene; Friedel-Crafts glycosidation (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...ontrolniKodProRIV
  • [531C9B3E16D6]
http://linked.open...v/mistoKonaniAkce
  • Český Krumlov
http://linked.open...i/riv/mistoVydani
  • Praha
http://linked.open...i/riv/nazevZdroje
  • Chemistry of Nucleic Acid Components
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...iv/tvurceVysledku
  • Bárta, Jan
  • Hocek, Michal
http://linked.open...vavai/riv/typAkce
http://linked.open...ain/vavai/riv/wos
  • 000257885700059
http://linked.open.../riv/zahajeniAkce
http://linked.open...n/vavai/riv/zamer
number of pages
http://purl.org/ne...btex#hasPublisher
  • Institute of Organic Chemistry and Biochemistry ASCR
https://schema.org/isbn
  • 978-80-86241-29-6
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