"B\u00E1rta, Jan" . . . "Praha" . . "2"^^ . "Modular synthesis of 5-substituted thiophen-2-yl C-2'-deoxyribonucleosides"@en . . "Chemistry of Nucleic Acid Components" . . "RIV/61388963:_____/08:00309912" . "A new modular methodology for the preparation of 5-substituted thiophen-2-yl C-nucleosides was developed. A Friedel\u2013Crafts-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 . . "2"^^ . . "000257885700059" . . . "Hocek, Michal" . "P(LC512), Z(AV0Z40550506)" . . "Institute of Organic Chemistry and Biochemistry ASCR" . . . "Byla vyvinuta nov\u00E1 modul\u00E1rn\u00ED metodika pro p\u0159\u00EDpravu 5-substituovan\u00FDch thiofen-2-yl C-nukleosid\u016F. Friedel-Crafts\u016Fv typ C-glykosidace 2-bromothiofenu s bis-toluoyl chr\u00E1n\u011Bn\u00FDm methylglykosidem poskytla po\u017Eadovan\u00FD 1-beta-(5-bromthiofen-2-yl)-1,2-dideoxyribofuranosid v 60% v\u00FDt\u011B\u017Eku. Odchr\u00E1n\u011Bn\u00ED toluoylovan\u00E9ho produktu poskytlo voln\u00FD bromthiofen C-nukleosid, kter\u00FD byl n\u00E1sledn\u011B ochr\u00E1n\u011Bn pomoc\u00ED TBDMS chr\u00E1nic\u00ED skupiny za vzniku bis-TBDMS chr\u00E1n\u011Bn\u00E9ho C-nukleosidu. Kl\u00ED\u010Dov\u00E9 chr\u00E1n\u011Bn\u00E9 C-nukleosidy byly pot\u00E9 vyu\u017Eity pro palladiem katalyzovan\u00E9 cross-coupling reakce. N\u00E1sledn\u00E9 vhodn\u00E9 odchr\u00E1n\u011Bn\u00ED produkt\u016F cross-coupling reakc\u00ED poskytlo s\u00E9ri\u00ED voln\u00FDch aryl a alkyl C-nukleosid\u016F. D\u00E1le byla vyzkou\u0161ena p\u0159\u00EDm\u00E1 p\u0159\u00EDprava voln\u00FDch C-nukleosid\u016F pomoc\u00ED Suzuki cross-coupling reakc\u00ED ve vodn\u00E9 f\u00E1zi, za pou\u017Eit\u00ED boronov\u00FDch kyselin a voln\u00E9ho bromthiofen C-nukleosidu."@cs . "[531C9B3E16D6]" . . "\u010Cesk\u00FD Krumlov" . "modular methodology; C-nucleosides; 5-bromothiophene; Friedel-Crafts glycosidation"@en . . "Modul\u00E1rn\u00ED synt\u00E9za 5-substituovan\u00FDch thiofen-2-yl C-2'-deoxyribonukleosid\u016F"@cs . "RIV/61388963:_____/08:00309912!RIV09-AV0-61388963" . . "Modular synthesis of 5-substituted thiophen-2-yl C-2'-deoxyribonucleosides" . "2008-06-08+02:00"^^ . . "A new modular methodology for the preparation of 5-substituted thiophen-2-yl C-nucleosides was developed. A Friedel\u2013Crafts-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." . "Modul\u00E1rn\u00ED synt\u00E9za 5-substituovan\u00FDch thiofen-2-yl C-2'-deoxyribonukleosid\u016F"@cs . "Modular synthesis of 5-substituted thiophen-2-yl C-2'-deoxyribonucleosides"@en . "978-80-86241-29-6" . "380266" . . . . "Modular synthesis of 5-substituted thiophen-2-yl C-2'-deoxyribonucleosides" . . "2"^^ .