136522-18-4

Upstream product

• 2304-96-3 N-benzyloxycarbonyl-L-asparagine 
• 136522-17-3 cis-N-butyldecahydro-2-<2(R)-hydroxy-4-phenyl-3(S)-aminobutyl>-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 50903-73-6 Z-Asn-OPfp 
• 147976-18-9 (4S,5S)-4-benzyl-2-oxo-oxazolidine-5-carboxylic acid 
• 162221-36-5 (4S,5S)-4-benzyl-2-oxo-oxazolidine-5-carboxylic acid methyl ether 
• 79261-58-8 (S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester 
• 124127-20-4 (S,S)-2-<2--1-hydroxy-3-phenylpropyl>-1,3-thiazole 
• 219586-42-2 2-<2(S)-(tert-Butoxyformamido)-1-hydroxy-3-phenylpropyl>thiazole 
• 72155-45-4 Boc-L-phenylalaninal 
• 1161-13-3 N-Cbz-L-Phe 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 149182-72-9 (S)-N-tert-butyl-1,2,3,4-tetrahydro-3-isoquinoline-carboxamide 
• 136465-78-6 N-tert-Butyldecahydro-2-(2(R)-hydroxy-4-phenyl-3(S)phthalimidobutyl)-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 136465-82-2 1-Hydroxy-4-phenyl-3(S)-phthalimido-2-butanone 

Downstream Products

• 127779-20-8 Saquinavir 
• 219959-35-0 N-tert.butyl-decahydro-2-[2-(R)-hydroxy-4-phenyl-3(S)-[{N-(2-[6-bromo]-quinolylcarbonyl)-L-asparaginyl}amino]butyl]-(4aS,8aS)-isoquinoline-3-carboxamide 
• 137431-06-2 2-[3(S)-[(L-asparaginyl)-amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert-butyl-decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel substitutedy-[1-benzyl-3-(3- tert-butylcarbamoyl-octahydroisoquinolin-2yl)-2-hydroxy-propyl] -2-[(2-oxo-2h-chromene-3-carbonyl) amino] succinamide analogs as anti-viral and anti-HIV agents

A series of novel substituted N1 [1-benzy1-3-(3-tert- butylcarbamoyloctahydroisoquinolin-2y1)-2-hydroxypropyl]-2-[(2-oxo-2H-chromene- 3-carbonyl) amino] succinamide analogs has been synthesized and evaluated for their anti-viral activity agains

Synthesis of the HIV-proteinase inhibitor Saquinavir: A challenge for process research

The task of process research, namely developing efficient, economically and technically as well as ecologically feasible syntheses in time, is demonstrated on the HIV-proteinase inhibitor Saquinavir (1), a complex molecule comprising six stereo-centres. Based on the first 26-step research synthesis furnishing a 10% overall yield, process research established a new, short 11-step synthesis affording a 50% overall yield.

Studies toward the Large-Scale Synthesis of the HIV Proteinase Inhibitor Ro 31-8959

Ro 31-8959 (1), a potent and selective inhibitor of HIV proteinase, is currently in phase III clinical trials.Six approaches for the large-scale synthesis of this compound have been studied.All routes employ an initial disconnection to an electrophilic L-phenylalanine homologue equivalent 13 and the decahydroisoquinoline derivative 5.They differ in adopting either an epoxide, a cyclic sulfate, or an aldehyde as the electrophilic entity and develop chirality from L-phenylalanine, dimethyl D-tartrate, or a Sharpless epoxidation.The preferred route starts from N-phthaloyl-L-phenylalaninyl chloride and uses tris((trimethylsilyl)oxy)ethene to effect homologation to hydroxy ketone 30, which is elaborated in a five-step two-pot procedure to N-phthaloyl epoxide 33 and hence 1.Kilogram quantities of Ro 31-8959 have been prepared using this route.