Stereoselective Synthesis of the Key Intermediates of the HIV Protease Inhibitor Fosamprenavir and Its Diastereomer

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F13%3A39896100" target="_blank" >RIV/00216275:25310/13:39896100 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1055/s-0033-1338803" target="_blank" >http://dx.doi.org/10.1055/s-0033-1338803</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1055/s-0033-1338803" target="_blank" >10.1055/s-0033-1338803</a>

Result language
angličtina
Original language name
Stereoselective Synthesis of the Key Intermediates of the HIV Protease Inhibitor Fosamprenavir and Its Diastereomer
Original language description
Highly stereoselective Henry reaction has been used in the synthesis of the fosamprenavir precursor (2S,3R)-N-tert-butyl-oxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane and its 2S, 3S diasteromer from N-tert-butyloxycarbonyl-(S)-phenylalaninal and nitromethane. The complex of (2S,5R)- or (2R,5S)-5-isopropyl-5-methyl-2-(pyridine-2-yl)imidazolidine-4-one with copper(II) acetate has been used as the catalyst which provided the product with 2S,3R absolute configuration (dr = 90: 10, overall yield 89%)or 2S,3S (dr = 99: 1, overall yield 94%), respectively.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/EE2.3.30.0021" target="_blank" >EE2.3.30.0021: Strenthening of Research and Development Teams at the University of Pardubice</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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