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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F12%3A10126876" target="_blank" >RIV/00216208:11310/12:10126876 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/12:00377774

Výsledek na webu

<a href="http://dx.doi.org/10.1002/ejoc.201101662" target="_blank" >http://dx.doi.org/10.1002/ejoc.201101662</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.201101662" target="_blank" >10.1002/ejoc.201101662</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/IAA400550902" target="_blank" >IAA400550902: Vývoj modulárních syntézy nových C-nukleosidů pro studium specificity DNA polymeras a rozšíření genetické abecedy</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2012

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Svazek periodika

neuveden

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

1759-1767

Kód UT WoS článku

000301445700015

EID výsledku v databázi Scopus

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