In a few simple steps starting from a commercially available reagents benzyl chloride and potassium thiocyanate, thiocyanate is obtained which is directly reacted with glycine amide to give benzyl thiourea. The used of concentrated HCl give the ring closed product of the latter. The alkylation of 3-benzyl-2- thioxoimidazolidin-4-one is made by the used of methyl iodide under basic condition. Subsequent treatment of the alkyl derivative 3-benzyl-2-(methylthio)-3,5dihydro-4-imidazole with diethyl phosphono cyanate gives the nitrile derivatives which upon treatment with sulphuric acid and functional group manipulations gave 1-benzyl-5-chloromethylimidazolium chloride. This compound is converted mildly under O'Donnell conditions into the l- Histidine derivative. After deprotection L-Histidine is obtained in good yield with 99% enantiomeric excess. This synthetic scheme allows access to any isotopomer of L-histidine and many other biologically important imidazole derivatives.
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Assistant professor Organic chemistry,Chemistry Department, Collage of Science, Al Imam Mohammad Ibn Saud Isalmic University Riyadh Saudi Arabia
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Taschenbuch. Zustand: Neu. A Novel Synthesis Of Isotopically Labelled L-Histidine | Sarra Talab | Taschenbuch | 120 S. | Englisch | 2019 | LAP LAMBERT Academic Publishing | EAN 9786139984787 | Verantwortliche Person für die EU: BoD - Books on Demand, In de Tarpen 42, 22848 Norderstedt, info[at]bod[dot]de | Anbieter: preigu. Artikel-Nr. 115183273
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Zustand: Hervorragend. Zustand: Hervorragend | Sprache: Englisch | Produktart: Bücher | In a few simple steps starting from a commercially available reagents benzyl chloride and potassium thiocyanate, thiocyanate is obtained which is directly reacted with glycine amide to give benzyl thiourea. The used of concentrated HCl give the ring closed product of the latter. The alkylation of 3-benzyl-2- thioxoimidazolidin-4-one is made by the used of methyl iodide under basic condition. Subsequent treatment of the alkyl derivative 3-benzyl-2-(methylthio)-3,5dihydro-4-imidazole with diethyl phosphono cyanate gives the nitrile derivatives which upon treatment with sulphuric acid and functional group manipulations gave 1-benzyl-5-chloromethylimidazolium chloride. This compound is converted mildly under O¿Donnell conditions into the l- Histidine derivative. After deprotection L-Histidine is obtained in good yield with 99% enantiomeric excess. This synthetic scheme allows access to any isotopomer of L-histidine and many other biologically important imidazole derivatives. Artikel-Nr. 33397896/1
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