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Statements

Subject Item
n2:RIV%2F61388963%3A_____%2F10%3A00350066%21RIV11-MSM-61388963
rdf:type
skos:Concept n16:Vysledek
dcterms:description
A new modular synthesis of diverse 2,4-disubstituted pyrimidin-5-yl C-2'-deoxyribonucleosides by sequential regioselective reactions of 2,6-dichloropyrimidin-5-yl C-nucleosides was developed. The intermediate was prepared by the Heck coupling of 2,6-dichloro-5-iodopyrimidine with glycal followed by desilylation and reduction. Its mild nucleophilic substitutions or Fe-catalyzed cross-coupling with MeMgCl proceeded regioselectively at position 4, whereas at elevated temperatures or with excess of MeMgCl, double substitution occurred. The 2-chloro-4-substituted intermediates undergo another substitution or coupling to afford 2,4-disubstituted derivatives. A new modular synthesis of diverse 2,4-disubstituted pyrimidin-5-yl C-2'-deoxyribonucleosides by sequential regioselective reactions of 2,6-dichloropyrimidin-5-yl C-nucleosides was developed. The intermediate was prepared by the Heck coupling of 2,6-dichloro-5-iodopyrimidine with glycal followed by desilylation and reduction. Its mild nucleophilic substitutions or Fe-catalyzed cross-coupling with MeMgCl proceeded regioselectively at position 4, whereas at elevated temperatures or with excess of MeMgCl, double substitution occurred. The 2-chloro-4-substituted intermediates undergo another substitution or coupling to afford 2,4-disubstituted derivatives.
dcterms:title
Synthesis of 2,4-Disubstituted Pyrimidin-5-yl C-2'-Deoxyribonucleosides by Sequential Regioselective Reactions of 2,4-Dichloropyrimidine Nucleosides Synthesis of 2,4-Disubstituted Pyrimidin-5-yl C-2'-Deoxyribonucleosides by Sequential Regioselective Reactions of 2,4-Dichloropyrimidine Nucleosides
skos:prefLabel
Synthesis of 2,4-Disubstituted Pyrimidin-5-yl C-2'-Deoxyribonucleosides by Sequential Regioselective Reactions of 2,4-Dichloropyrimidine Nucleosides Synthesis of 2,4-Disubstituted Pyrimidin-5-yl C-2'-Deoxyribonucleosides by Sequential Regioselective Reactions of 2,4-Dichloropyrimidine Nucleosides
skos:notation
RIV/61388963:_____/10:00350066!RIV11-MSM-61388963
n4:aktivita
n15:P n15:Z
n4:aktivity
P(IAA400550902), P(LC512), Z(AV0Z40550506)
n4:cisloPeriodika
14
n4:dodaniDat
n9:2011
n4:domaciTvurceVysledku
n5:3839664 n5:6659160 n5:8591083 n5:7345828
n4:druhVysledku
n11:J
n4:duvernostUdaju
n17:S
n4:entitaPredkladatele
n10:predkladatel
n4:idSjednocenehoVysledku
291557
n4:idVysledku
RIV/61388963:_____/10:00350066
n4:jazykVysledku
n12:eng
n4:klicovaSlova
C-nucleosides; pyrimidines; cross-coupling
n4:klicoveSlovo
n13:cross-coupling n13:pyrimidines n13:C-nucleosides
n4:kodStatuVydavatele
DE - Spolková republika Německo
n4:kontrolniKodProRIV
[F13D1309C37F]
n4:nazevZdroje
European Journal of Organic Chemistry
n4:obor
n7:CC
n4:pocetDomacichTvurcuVysledku
4
n4:pocetTvurcuVysledku
4
n4:projekt
n6:IAA400550902 n6:LC512
n4:rokUplatneniVysledku
n9:2010
n4:svazekPeriodika
-
n4:tvurceVysledku
Kubelka, Tomáš Slavětínská, Lenka Hocek, Michal Klepetářová, Blanka
n4:wos
000277928600004
n4:zamer
n18:AV0Z40550506
s:issn
1434-193X
s:numberOfPages
4