About: Synthesis of 6-Substituted 2(1H)-Pyridon-3-yl C-2'-Deoxyribonucleosides

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About: Synthesis of 6-Substituted 2(1H)-Pyridon-3-yl C-2'-Deoxyribonucleosides Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
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. (en)
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 (en)
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 (en)
skos:notation	RIV/61388963:_____/12:00377774!RIV13-AV0-61388963
http://linked.open...avai/predkladatel	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...avai/riv/aktivita	I P Z
http://linked.open...avai/riv/aktivity	I, P(IAA400550902), Z(AV0Z40550506)
http://linked.open...iv/cisloPeriodika	9
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Pohl, Radek Hocek, Michal Kubelka, Tomáš Joubert, Nicolas Chapuis, Hubert Jean
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	173000
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/12:00377774
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	nucleosides; pyridones; cross-coupling; Heck reaction (en)
http://linked.open.../riv/klicoveSlovo	Heck reaction cross-coupling nucleosides pyridones
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[155DC6A8F057]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	5 (xsd:int)
http://linked.open...cetTvurcuVysledku	5 (xsd:int)
http://linked.open...vavai/riv/projekt	Development of modular syntheses of new C-nucleosides for studying DNA polymerase specificity and for the extension of the genetic alphabet
http://linked.open...UplatneniVysledku	2012
http://linked.open...iv/tvurceVysledku	Hocek, Michal Joubert, Nicolas Pohl, Radek Kubelka, Tomáš Chapuis, Hubert Jean
http://linked.open...ain/vavai/riv/wos	000301445700015
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství
issn	1434-193X
number of pages	9 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/ejoc.201101662
is http://linked.open...avai/riv/vysledek of	Synthesis of 6-Substituted 2(1H)-Pyridon-3-yl C-2'-Deoxyribonucleosides

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