About: Microwave-assisted hydrolysis of phosphonate diesters: an efficient protocol for the preparation of phosphonic acids

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	A new highly efficient method for the hydrolysis of acyclic nucleoside phosphonate diesters (or generally of any organophosphonates) to the corresponding phosphonic acids has been developed. This novel methodology employs inexpensive hydrochloric acid in equimolar amounts to the number of ester groups present in the molecule and thus, avoids using trimethylsilyl halogenides, the standard reagents for these types of transformations. Moreover, simple and easy work-up of the reaction mixture affords very clean products in high yields (usually 77-93%). Another advantage of the described hydrolysis of phosphonate diesters is the fact that the course of the reaction can be instantly monitored through pressure changes in the reaction vessel. This 'green' method has also been successfully used for the preparation of otherwise synthetically difficult to access (phosphonomethoxy) ethyl (PME) derivatives of guanine (PMEG) and hypoxanthine (PMEHx), and furthermore, the method gains access to important novel acyclic nucleoside phosphonates derived from 2-chlorohypoxanthine and from xanthine (e.g. PMEX). A new highly efficient method for the hydrolysis of acyclic nucleoside phosphonate diesters (or generally of any organophosphonates) to the corresponding phosphonic acids has been developed. This novel methodology employs inexpensive hydrochloric acid in equimolar amounts to the number of ester groups present in the molecule and thus, avoids using trimethylsilyl halogenides, the standard reagents for these types of transformations. Moreover, simple and easy work-up of the reaction mixture affords very clean products in high yields (usually 77-93%). Another advantage of the described hydrolysis of phosphonate diesters is the fact that the course of the reaction can be instantly monitored through pressure changes in the reaction vessel. This 'green' method has also been successfully used for the preparation of otherwise synthetically difficult to access (phosphonomethoxy) ethyl (PME) derivatives of guanine (PMEG) and hypoxanthine (PMEHx), and furthermore, the method gains access to important novel acyclic nucleoside phosphonates derived from 2-chlorohypoxanthine and from xanthine (e.g. PMEX). (en)
Title	Microwave-assisted hydrolysis of phosphonate diesters: an efficient protocol for the preparation of phosphonic acids Microwave-assisted hydrolysis of phosphonate diesters: an efficient protocol for the preparation of phosphonic acids (en)
skos:prefLabel	Microwave-assisted hydrolysis of phosphonate diesters: an efficient protocol for the preparation of phosphonic acids Microwave-assisted hydrolysis of phosphonate diesters: an efficient protocol for the preparation of phosphonic acids (en)
skos:notation	RIV/61388963:_____/12:00380396!RIV13-AV0-61388963
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(VG20102015046), Z(AV0Z40550506)
http://linked.open...iv/cisloPeriodika	8
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Baszczyňski, Ondřej Jansa, Petr Janeba, Zlatko Dračínský, Martin Procházková, Eliška
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	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	150453
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/12:00380396
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	acyclic nucleoside phosphonates; DNA virus; retrovirus infections; cidofovir; organic-synthesis (en)
http://linked.open.../riv/klicoveSlovo	DNA virus retrovirus infections organic-synthesis acyclic nucleoside phosphonates cidofovir
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[3EB3C74380DC]
http://linked.open...i/riv/nazevZdroje	Green Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	5 (xsd:int)
http://linked.open...cetTvurcuVysledku	5 (xsd:int)
http://linked.open...vavai/riv/projekt	Targeted drug design for bioterrorism prevention. Development of effective inhibitors of the adenylate cyclase toxin of Bordetella pertusis and Bacillus anthracis.
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	14
http://linked.open...iv/tvurceVysledku	Baszczyňski, Ondřej Dračínský, Martin Janeba, Zlatko Jansa, Petr Procházková, Eliška
http://linked.open...ain/vavai/riv/wos	000306658200028
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství
issn	1463-9262
number of pages	7 (xsd:int)
http://bibframe.org/vocab/doi	10.1039/c2gc35547g

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