Original title: Synthesis of (purin-6-yl)acetates and their transformations
Translated title: Syntéza (purin-6-yl)acetátů a jejich transformace
Authors: Hasník, Zbyněk ; Hocek, Michal
Document type: Papers
Conference/Event: Symposium on Chemistry of Nucleic Acid Components /14./, Český Krumlov (CZ), 2008-06-08 / 2008-06-13
Year: 2008
Language: eng
Abstract: [eng] [cze]
A novel approach to the synthesis of (purin-6-yl)acetates was developed based on Pd-catalysed cross-coupling reactions of 6-chloropurines with the Reformatsky agent. These intermediates were converted into various products by functional group transformations. Amides were prepared by amidation of ester group with amines, 6-(hydroxyethyl)purines by reduction by NaBH4, and beta-substituted 6-ethylpurines by mesylation of 6-(hydroxyethyl)purines and subsequent nucleophilic substitution. Byla vyvinut nový přístup k syntéze (purin-6-yl)acetátů založen na palladiem katalyzovaných cross-coupling reakcích 6-chlorpurinu s Reformackého činidlem. Tyto intermediáty byly přeměněny na další látky transformacemi funkčních skupin. Amidy byly připraveny amidacemi esterové skupiny, 6-(hydroxyethyl)puriny byly redukovány pomocí NaBH4, a beta-substituované 6-ethylpuriny byly připraveny mesylací 6-(hydroxyethyl)purinů a jejich následnou nukleofilní substitucí.
Keywords: cross-coupling; nucleosides; purines
Project no.: CEZ:AV0Z40550506 (CEP), 1M0508 (CEP), 1QS400550501 (CEP)
Funding provider: GA MŠk, GA AV ČR
Host item entry: Chemistry of Nucleic Acid Components, ISBN 978-80-86241-29-6

Institution: Institute of Organic Chemistry and Biochemistry AS ČR (web)
Document availability information: Fulltext is available at the institute of the Academy of Sciences.
Original record: http://hdl.handle.net/11104/0161936

Permalink: http://www.nusl.cz/ntk/nusl-38965


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Research > Institutes ASCR > Institute of Organic Chemistry and Biochemistry
Conference materials > Papers