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Statements

Subject Item
n2:RIV%2F61388963%3A_____%2F12%3A00377774%21RIV13-AV0-61388963
rdf:type
skos:Concept n10:Vysledek
dcterms:description
Two approaches to the synthesis of the title 6-substituted 2(1H)-pyridon-3-yl C-2-deoxyribonucleosides have been pursued. A protected 6-aminopyridine C-nucleoside intermediate was converted into the N-oxide followed by rearrangement and deprotection to give 6-acetylamino-2-oxo(1H)-pyridin-3-yl deoxyribonucleoside. Due to the unusually high stability of the N-acetyl group, the full deprotection was unsuccessful. In the second approach, 6-chloro-2-pyridone was converted into phosphorodiamidate, which underwent ortho-magnesiation and iodination to give the 3-iododerivative. It was then used in a Heck coupling with a sugar glycal and the resulting product deprotected to give 6-chloro-2-oxo(1H)-pyridin-3-yl deoxyribonucleoside, which was converted into 6-methyl-, 6-amino-, and 6-unsubstituted pyridone C-nucleosides. The final nucleosides were very unstable which limits their further use in chemical biology. Two approaches to the synthesis of the title 6-substituted 2(1H)-pyridon-3-yl C-2-deoxyribonucleosides have been pursued. A protected 6-aminopyridine C-nucleoside intermediate was converted into the N-oxide followed by rearrangement and deprotection to give 6-acetylamino-2-oxo(1H)-pyridin-3-yl deoxyribonucleoside. Due to the unusually high stability of the N-acetyl group, the full deprotection was unsuccessful. In the second approach, 6-chloro-2-pyridone was converted into phosphorodiamidate, which underwent ortho-magnesiation and iodination to give the 3-iododerivative. It was then used in a Heck coupling with a sugar glycal and the resulting product deprotected to give 6-chloro-2-oxo(1H)-pyridin-3-yl deoxyribonucleoside, which was converted into 6-methyl-, 6-amino-, and 6-unsubstituted pyridone C-nucleosides. The final nucleosides were very unstable which limits their further use in chemical biology.
dcterms:title
Synthesis of 6-Substituted 2(1H)-Pyridon-3-yl C-2'-Deoxyribonucleosides Synthesis of 6-Substituted 2(1H)-Pyridon-3-yl C-2'-Deoxyribonucleosides
skos:prefLabel
Synthesis of 6-Substituted 2(1H)-Pyridon-3-yl C-2'-Deoxyribonucleosides Synthesis of 6-Substituted 2(1H)-Pyridon-3-yl C-2'-Deoxyribonucleosides
skos:notation
RIV/61388963:_____/12:00377774!RIV13-AV0-61388963
n10:predkladatel
n15:ico%3A61388963
n3:aktivita
n8:P n8:Z n8:I
n3:aktivity
I, P(IAA400550902), Z(AV0Z40550506)
n3:cisloPeriodika
9
n3:dodaniDat
n4:2013
n3:domaciTvurceVysledku
n6:8591083 Chapuis, Hubert Jean n6:6659160 n6:3603652 Joubert, Nicolas
n3:druhVysledku
n20:J
n3:duvernostUdaju
n19:S
n3:entitaPredkladatele
n12:predkladatel
n3:idSjednocenehoVysledku
173000
n3:idVysledku
RIV/61388963:_____/12:00377774
n3:jazykVysledku
n9:eng
n3:klicovaSlova
nucleosides; pyridones; cross-coupling; Heck reaction
n3:klicoveSlovo
n5:nucleosides n5:cross-coupling n5:pyridones n5:Heck%20reaction
n3:kodStatuVydavatele
DE - Spolková republika Německo
n3:kontrolniKodProRIV
[155DC6A8F057]
n3:nazevZdroje
European Journal of Organic Chemistry
n3:obor
n13:CC
n3:pocetDomacichTvurcuVysledku
5
n3:pocetTvurcuVysledku
5
n3:projekt
n18:IAA400550902
n3:rokUplatneniVysledku
n4:2012
n3:tvurceVysledku
Joubert, Nicolas Kubelka, Tomáš Pohl, Radek Chapuis, Hubert Jean Hocek, Michal
n3:wos
000301445700015
n3:zamer
n16:AV0Z40550506
s:issn
1434-193X
s:numberOfPages
9
n17:doi
10.1002/ejoc.201101662