174302-74-0

Upstream product

• 75-52-5 nitromethane 
• 72155-45-4 Boc-L-phenylalaninal 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 174302-72-8 (S)-3-tert-butoxycarbonylamino-1-nitro-4-phenyl-2-butanone 

Downstream Products

• 1422207-68-8 C₃₃H₄₃N₃O₃ 
• 162541-34-6 ((1S,2S)-3-Amino-1-benzyl-2-hydroxy-propyl)-carbamic acid tert-butyl ester 
• 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 

Relevant academic research and scientific papers

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.

Stereoselective synthesis of the key intermediates of the HIV protease inhibitor fosamprenavir and its diastereomer

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

Formation of multi-stereogenic centers using a catalytic diastereoselective Henry reaction

A diastereoselective Henry reaction of chiral aldehydes with nitroalkanes was developed using a chiral sulfonyldiamine (L1)-CuCl complex. The reaction of (R)-2-phenylpropanal and nitromethane was smoothly catalyzed by the (S,S,S)-L1-CuCl complex to give the adduct with 99/1 syn/anti selectivity in 99% ee. In the reaction of (S)-2-phenylpropanal and nitroethane, the (R,R,R)-L1-CuCl catalyst yielded the expected three contiguous stereogenic centers in a highly syn-selective Henry reaction.

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.

Diastereoselective catalytic asymmetric nitroaldol reaction utilizing rare earth-Li-(R)-BINOL complex. A highly efficient synthesis of norstatine

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