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Description
| - 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)
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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)
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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)
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skos:notation
| - RIV/61388963:_____/08:00309912!RIV09-AV0-61388963
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http://linked.open...avai/riv/aktivita
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http://linked.open...avai/riv/aktivity
| - P(LC512), Z(AV0Z40550506)
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http://linked.open...vai/riv/dodaniDat
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http://linked.open...aciTvurceVysledku
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http://linked.open.../riv/druhVysledku
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http://linked.open...iv/duvernostUdaju
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http://linked.open...titaPredkladatele
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http://linked.open...dnocenehoVysledku
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http://linked.open...ai/riv/idVysledku
| - RIV/61388963:_____/08:00309912
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http://linked.open...riv/jazykVysledku
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http://linked.open.../riv/klicovaSlova
| - modular methodology; C-nucleosides; 5-bromothiophene; Friedel-Crafts glycosidation (en)
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http://linked.open.../riv/klicoveSlovo
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http://linked.open...ontrolniKodProRIV
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http://linked.open...v/mistoKonaniAkce
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http://linked.open...i/riv/mistoVydani
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http://linked.open...i/riv/nazevZdroje
| - Chemistry of Nucleic Acid Components
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http://linked.open...in/vavai/riv/obor
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http://linked.open...ichTvurcuVysledku
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http://linked.open...cetTvurcuVysledku
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http://linked.open...vavai/riv/projekt
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http://linked.open...UplatneniVysledku
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http://linked.open...iv/tvurceVysledku
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http://linked.open...vavai/riv/typAkce
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http://linked.open...ain/vavai/riv/wos
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http://linked.open.../riv/zahajeniAkce
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http://linked.open...n/vavai/riv/zamer
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number of pages
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http://purl.org/ne...btex#hasPublisher
| - Institute of Organic Chemistry and Biochemistry ASCR
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https://schema.org/isbn
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