- Stereoselective synthesis of the key intermediates of the HIV protease inhibitor fosamprenavir and its diastereomer
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Highly stereoselective Henry reaction has been used in the synthesis of the fosamprenavir precursor (2S,3R)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1- phenyl-4-nitrobutane and its 2S,3S diasteromer from N-tert-butyloxycarbonyl-(S)- phenylalaninal and ni
- Panov, Illia,Drabina, Pavel,Hanusek, Ji?í,Sedlák, Milo?
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- Intermediate reaches reed that Wei new synthetic process of the
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The invention provides a novel synthesis process of Darunavir intermediate, N-tertbutyloxycarbonyl-L-phenylalanine is used as a raw material, esterification, condensation, reduction, hydrogenation and reduction amination, and other reactions are carried out for preparing the key intermediate of Darunavir: (2R,3S)-3-(tert-butyloxycarbonyl)amino-1-[(2-methyl propyl)amino]-4-phenyl-2-butanol. The new synthesis process of Darunavir intermediate has the advantages of mild reaction condition, simple operation, and high reaction selectivity and yield, and the process is suitable for industrial production.
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- re- and si-face-selective nitroaldol reactions catalyzed by a rigid chiral quaternary ammonium salt: A highly stereoselective synthesis of the HIV protease inhibitor amprenavir (Vertex 478)
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Either amprenavir (1) or its C(2) diastereomer can be synthesized in a simple way by the use of a nitroaldol reaction carried out in the presence of one or the other of the two ammonium ions 2. The 1,3-diamino-2-hydroxypropyl structural element of 1 is also found in many other peptidomimetics and HIV protease inhibitors. Described here is a new strategy for possible application to direct and stereocontrolled synthesis of such compounds.
- Corey,Zhang, Fu-Yao
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p. 1931 - 1934
(2007/10/03)
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- A facile synthesis of (2R,3S)-1-amino-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutane; A useful component block of HIV protease inhibitor
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(S)-3-tert-Butoxycarbonylamino-1-nitro-2-oxo-4-phenylbutane 4 was converted to (2R,3S)-1-amino-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutane 5a by a catalytic hydrogenation, or NaBH4-TiCl4 reduction followed by hydrogenation in favorable diastereoselectivity, a component of the HIV protease inhibitor VX-478.
- Yuasa, Yoko,Yuasa, Yoshifumi,Tsuruta, Haruki
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p. 395 - 401
(2007/10/03)
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- Diastereoselective catalytic asymmetric nitroaldol reaction utilizing rare earth-Li-(R)-BINOL complex. A highly efficient synthesis of norstatine
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Rare earth-Li-BINOL complexes were used to catalyze nitroaldol reactions of optically active α-amino-aldehydes with nitromethane in a highly diastereoselective manner. A typical adduct, (2S, 3S)-3-phtaloylamino-2-hydroxy-1-nitro-4-phenylbutane was conveni
- Sasai,Sasai, Hiroaki,Kim,Kim, Won-Sup,Suzuki,Suzuki, Takeyuki,Shibasaki,Shibasaki, Masakatsu,Mitsuda,Mitsuda, Masaru,Hasegawa,Hasegawa, Junzo,Ohashi,Ohashi, Takehisa
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p. 6123 - 6126
(2007/10/02)
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