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Statements

Subject Item
n2:RIV%2F60461373%3A22310%2F12%3A43892738%21RIV13-GA0-22310___
rdf:type
n9:Vysledek skos:Concept
dcterms:description
9-Boc-6-chloropurine, which can be obtained in high yield, is nearly quantitatively reduced with the THF?BH3 complex. The obtained 9-Boc-7,8-dihydropurine derivative is more stable compared to the corresponding 9-tritylpurine and can be smoothly N7-alkylated, acylated, or it can serve as an N-nucleophile in conjugate additions. Deprotection with trifluoroacetic acid followed by MnO2 oxidation affords the N7-substituted purines in high yields. The whole sequence of alkylation, deprotection, and oxidation can be done with crude intermediates using chromatography only for the purification of the final N7-substituted purine. 9-Boc-6-chloropurine, which can be obtained in high yield, is nearly quantitatively reduced with the THF?BH3 complex. The obtained 9-Boc-7,8-dihydropurine derivative is more stable compared to the corresponding 9-tritylpurine and can be smoothly N7-alkylated, acylated, or it can serve as an N-nucleophile in conjugate additions. Deprotection with trifluoroacetic acid followed by MnO2 oxidation affords the N7-substituted purines in high yields. The whole sequence of alkylation, deprotection, and oxidation can be done with crude intermediates using chromatography only for the purification of the final N7-substituted purine.
dcterms:title
Highly Efficient and Broad-Scope Protocol for the Preparation of 7-Substituted 6-Halopurines via N9-Boc-Protected 7,8-Dihydropurines Highly Efficient and Broad-Scope Protocol for the Preparation of 7-Substituted 6-Halopurines via N9-Boc-Protected 7,8-Dihydropurines
skos:prefLabel
Highly Efficient and Broad-Scope Protocol for the Preparation of 7-Substituted 6-Halopurines via N9-Boc-Protected 7,8-Dihydropurines Highly Efficient and Broad-Scope Protocol for the Preparation of 7-Substituted 6-Halopurines via N9-Boc-Protected 7,8-Dihydropurines
skos:notation
RIV/60461373:22310/12:43892738!RIV13-GA0-22310___
n9:predkladatel
n13:orjk%3A22310
n4:aktivita
n19:S n19:P
n4:aktivity
P(GA203/09/1552), P(LC06070), S
n4:cisloPeriodika
4
n4:dodaniDat
n12:2013
n4:domaciTvurceVysledku
n10:5078008 n10:6702198 n10:3809684
n4:druhVysledku
n20:J
n4:duvernostUdaju
n5:S
n4:entitaPredkladatele
n16:predkladatel
n4:idSjednocenehoVysledku
139008
n4:idVysledku
RIV/60461373:22310/12:43892738
n4:jazykVysledku
n15:eng
n4:klicovaSlova
reduction; nucleobases; Michael addition; acylation; alkylation
n4:klicoveSlovo
n11:Michael%20addition n11:reduction n11:alkylation n11:nucleobases n11:acylation
n4:kodStatuVydavatele
DE - Spolková republika Německo
n4:kontrolniKodProRIV
[2B7E3932905E]
n4:nazevZdroje
Synthesis
n4:obor
n14:CC
n4:pocetDomacichTvurcuVysledku
3
n4:pocetTvurcuVysledku
3
n4:projekt
n6:LC06070 n6:GA203%2F09%2F1552
n4:rokUplatneniVysledku
n12:2012
n4:svazekPeriodika
44
n4:tvurceVysledku
Dvořák, Dalimil Kotek, Vladislav Tobrman, Tomáš
s:issn
0039-7881
s:numberOfPages
8
n18:doi
10.1055/s-0031-1290068
n17:organizacniJednotka
22310