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

Result code in 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>

Alternative codes found

RIV/61388963:_____/12:00377774

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language 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.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/IAA400550902" target="_blank" >IAA400550902: Development of modular syntheses of new C-nucleosides for studying DNA polymerase specificity and for the extension of the genetic alphabet</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2012

Confidentiality

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

Name of the periodical

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Volume of the periodical

neuveden

Issue of the periodical within the volume

9

Country of publishing house

DE - GERMANY

Number of pages

9

Pages from-to

1759-1767

UT code for WoS article

000301445700015

EID of the result in the Scopus database

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