162541-34-6

Upstream product

• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 174302-72-8 (S)-3-tert-butoxycarbonylamino-1-nitro-4-phenyl-2-butanone 
• 174302-74-0 (2S,3S)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane 
• 1385766-21-1 tert-butyl (2S,3S)-4-azido-3-hydroxy-1-phenylbutan-2-ylcarbamate 
• 72155-45-4 Boc-L-phenylalaninal 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 60398-41-6 (3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate 
• 67729-36-6 Boc-Phe-O-COO-isoBu 
• 102123-74-0 (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 
• 162536-40-5 (2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane 

Downstream Products

• 1005323-79-4 C₂₁H₂₇N₃O₇S 
• 192800-79-6 4-amino-N-((2S,3S)-2-hydroxy-4-phenyl-3-amino-butyl)-N-isobutyl-benzenesulfonamide 
• 143225-31-4 (2S,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1-(isobutylamino)-4-phenylbutan-2-ol 
• 161302-38-1 (1S-(1R*,2R)(3S*))-<3-<<3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-hydroxy-4-phenylbutyl>amino>-2-hydroxy-1-(phenylmethyl)propyl>carbamic acid 1,1-dimethylethyl ester 

Relevant academic research and scientific papers

BISFURANYL PROTEASE INHIBITORS

The present invention provides compounds of Formula (I): wherein A, X, Q, R2-R6, m, and W have the values described herein, as well as compositions comprising such compounds. The compounds are protease inhibitors and are useful for i

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)

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.

A facile synthesis of (2R,3S)-1-amino-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutane; A useful component block of HIV protease inhibitor

(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.

Aminodiol HIV Protease Inhibitors. 1. Design, Synthesis, and Preliminary SAR

A series of HIV protease inhibitors containing a novel C2 symmetrical "aminodiol" core structure were prepared from amino acid starting materials.The ability of the aminodiols to inhibit HIV replication in cell culture is comparable to their ability to inhibit the isolated enzyme, a result compatible with good cell membrane penetration by this class of compounds.Optimization of the structure-activity in this series led to aminodiol 9a (Ki = 100 nM; ED50(HIV-1) = 80 nM) containing P1/P1' benzyl and P2/P2' Boc substituents.Compound 9a is a selective inhibito r of HIV protease versus other aspartyl proteases such as human renin, human cathepsin D, and porcine pepsin.In addition, 9a is equipotent against HIV-1 and HIV-2 in cell culture and demonstrates similar activity in infected T-lymphocytes and PBMCs.After iv and oral administration in rats, 9a displayed significant oral bioavailability (ca. 40percent) and a promising plasma elimination half-life (4 h).