About: Stereoselective Synthesis of the Key Intermediates of the HIV Protease Inhibitor Fosamprenavir and Its Diastereomer     Goto   Sponge   NotDistinct   Permalink

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  • 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.
  • 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. (en)
Title
  • Stereoselective Synthesis of the Key Intermediates of the HIV Protease Inhibitor Fosamprenavir and Its Diastereomer
  • Stereoselective Synthesis of the Key Intermediates of the HIV Protease Inhibitor Fosamprenavir and Its Diastereomer (en)
skos:prefLabel
  • Stereoselective Synthesis of the Key Intermediates of the HIV Protease Inhibitor Fosamprenavir and Its Diastereomer
  • Stereoselective Synthesis of the Key Intermediates of the HIV Protease Inhibitor Fosamprenavir and Its Diastereomer (en)
skos:notation
  • RIV/00216275:25310/13:39896100!RIV14-MSM-25310___
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  • P(EE2.3.30.0021)
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  • 10
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  • 107954
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  • RIV/00216275:25310/13:39896100
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  • ligands; homogenous catalysis; HIV; diastereoselectivity; aldol reaction (en)
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  • DE - Spolková republika Německo
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  • [1D7304E5C4CD]
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  • 24
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  • Drabina, Pavel
  • Panov, Illia
  • Sedlák, Miloš
  • Hanusek, Jiří
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  • 000320576300023
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  • 0936-5214
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  • 10.1055/s-0033-1338803
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  • 25310
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