About: Highly Efficient and Broad-Scope Protocol for the Preparation of 7-Substituted 6-Halopurines via N9-Boc-Protected 7,8-Dihydropurines

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About: Highly Efficient and Broad-Scope Protocol for the Preparation of 7-Substituted 6-Halopurines via N9-Boc-Protected 7,8-Dihydropurines Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
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. (en)
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 (en)
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 (en)
skos:notation	RIV/60461373:22310/12:43892738!RIV13-GA0-22310___
http://linked.open...avai/riv/aktivita	P S
http://linked.open...avai/riv/aktivity	P(GA203/09/1552), P(LC06070), S
http://linked.open...iv/cisloPeriodika	4
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Dvořák, Dalimil Tobrman, Tomáš Kotek, Vladislav
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	Vysoká škola chemicko-technologická v Praze / Fakulta chemické technologie
http://linked.open...dnocenehoVysledku	139008
http://linked.open...ai/riv/idVysledku	RIV/60461373:22310/12:43892738
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	reduction; nucleobases; Michael addition; acylation; alkylation (en)
http://linked.open.../riv/klicoveSlovo	acylation nucleobases Michael addition reduction alkylation
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[2B7E3932905E]
http://linked.open...i/riv/nazevZdroje	Synthesis
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...vavai/riv/projekt	Application of 7,8-Dihydropurines in the Synthesis of New Purine Derivatives with Potential Biological Activity The structure and synthetic applications of transition metal complexes
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	44
http://linked.open...iv/tvurceVysledku	Dvořák, Dalimil Tobrman, Tomáš Kotek, Vladislav
issn	0039-7881
number of pages	8 (xsd:int)
http://bibframe.org/vocab/doi	10.1055/s-0031-1290068
http://localhost/t...ganizacniJednotka	22310

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