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Statements

Subject Item
n2:RIV%2F61388963%3A_____%2F11%3A00364189%21RIV12-AV0-61388963
rdf:type
skos:Concept n15:Vysledek
dcterms:description
A general modular and practical methodology for preparation of diverse 5-substituted pyridin-2-yl and 6-substituted pyridin-3-yl C-ribonucleosides was developed. Regioselective lithiation of 2,5-dibromopyridine proceeded at the position 5- or 2- depending on the solvent and the resulting bromopyridyl lithium species underwent additions to protected ribonolactone and further transformations to hemiketals that were diastereoselectively reduced to give either 5-bromopyridine-2-yl or 6-bromopyridine-3-yl silyl-protected C-ribonucleosides. These intermediates were then subjected to a series of cross-coupling reactions, aminations, aminocarbonylations and hydroxylations to give a series of protected 1beta-(5-alkyl-, 5-aryl-, 5-amino- 5-carbamoyl and 5-hydroxypyridin-2-yl)-C-ribonucleosides and beta-(6-alkyl-, 6-aryl-, 6-amino- 6-carbamoyl and 6-hydroxypyridin-3-yl)-C-ribonucleosides. Deprotection of silylated nucleosides by Et3N.3HF, TBAF or TFA gave a series of free C-nucleosides. A general modular and practical methodology for preparation of diverse 5-substituted pyridin-2-yl and 6-substituted pyridin-3-yl C-ribonucleosides was developed. Regioselective lithiation of 2,5-dibromopyridine proceeded at the position 5- or 2- depending on the solvent and the resulting bromopyridyl lithium species underwent additions to protected ribonolactone and further transformations to hemiketals that were diastereoselectively reduced to give either 5-bromopyridine-2-yl or 6-bromopyridine-3-yl silyl-protected C-ribonucleosides. These intermediates were then subjected to a series of cross-coupling reactions, aminations, aminocarbonylations and hydroxylations to give a series of protected 1beta-(5-alkyl-, 5-aryl-, 5-amino- 5-carbamoyl and 5-hydroxypyridin-2-yl)-C-ribonucleosides and beta-(6-alkyl-, 6-aryl-, 6-amino- 6-carbamoyl and 6-hydroxypyridin-3-yl)-C-ribonucleosides. Deprotection of silylated nucleosides by Et3N.3HF, TBAF or TFA gave a series of free C-nucleosides.
dcterms:title
General and Modular Synthesis of Isomeric 5-Substituted Pyridin-2-yl and 6-Substituted Pyridin-3-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Hetaryl, Amino, Carbamoyl, and Hydroxy Groups General and Modular Synthesis of Isomeric 5-Substituted Pyridin-2-yl and 6-Substituted Pyridin-3-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Hetaryl, Amino, Carbamoyl, and Hydroxy Groups
skos:prefLabel
General and Modular Synthesis of Isomeric 5-Substituted Pyridin-2-yl and 6-Substituted Pyridin-3-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Hetaryl, Amino, Carbamoyl, and Hydroxy Groups General and Modular Synthesis of Isomeric 5-Substituted Pyridin-2-yl and 6-Substituted Pyridin-3-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Hetaryl, Amino, Carbamoyl, and Hydroxy Groups
skos:notation
RIV/61388963:_____/11:00364189!RIV12-AV0-61388963
n15:predkladatel
n17:ico%3A61388963
n3:aktivita
n11:Z n11:P
n3:aktivity
P(IAA400550902), P(LC512), Z(AV0Z40550506)
n3:cisloPeriodika
16
n3:dodaniDat
n13:2012
n3:domaciTvurceVysledku
n9:6659160 n9:3839664 n9:7345828 n9:5136695
n3:druhVysledku
n16:J
n3:duvernostUdaju
n12:S
n3:entitaPredkladatele
n20:predkladatel
n3:idSjednocenehoVysledku
200892
n3:idVysledku
RIV/61388963:_____/11:00364189
n3:jazykVysledku
n18:eng
n3:klicovaSlova
nucleosides; palladium-catalyzed amination; C-2'-deoxyribonucleosides; cytidine; benzene
n3:klicoveSlovo
n4:cytidine n4:nucleosides n4:C-2%27-deoxyribonucleosides n4:benzene n4:palladium-catalyzed%20amination
n3:kodStatuVydavatele
US - Spojené státy americké
n3:kontrolniKodProRIV
[264332C8FDFE]
n3:nazevZdroje
Journal of Organic Chemistry
n3:obor
n10:CC
n3:pocetDomacichTvurcuVysledku
4
n3:pocetTvurcuVysledku
4
n3:projekt
n14:IAA400550902 n14:LC512
n3:rokUplatneniVysledku
n13:2011
n3:svazekPeriodika
76
n3:tvurceVysledku
Klepetářová, Blanka Hocek, Michal Slavětínská, Lenka Štefko, Martin
n3:wos
000293759000016
n3:zamer
n6:AV0Z40550506
s:issn
0022-3263
s:numberOfPages
17
n5:doi
10.1021/jo200949c