136522-18-4

Basic information

• Product Name: benzyl [(2S)-4-amino-1-({(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-yl}amino)-1,4-dioxobutan-2-yl]carbamate (non-preferred name)
• Synonyms: carbamic acid, N-[(1S)-3-amino-1-[[[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]amino]carbonyl]-3-oxopropyl]-, phenylmethyl ester
• CAS NO: 136522-18-4
• Molecular Formula: C₃₆H₅₁N₅O₆
• Molecular Weight: 649.82
• Mol File: 136522-18-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 935.5°C at 760 mmHg
• Flash Point: 519.6°C
• Density: 1.186g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: benzyl [(2S)-4-amino-1-({(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-yl}amino)-1,4-dioxobutan-2-yl]carbamate (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl [(2S)-4-amino-1-({(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-yl}amino)-1,4-dioxobutan-2-yl]carbamate (non-preferred name)(136522-18-4)
• EPA Substance Registry System: benzyl [(2S)-4-amino-1-({(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-yl}amino)-1,4-dioxobutan-2-yl]carbamate (non-preferred name)(136522-18-4)

Safety Data

• Hazardous Substances Data: 136522-18-4(Hazardous Substances Data)

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 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 149182-71-8 benzyl 3(S)-(t-butylcarbamoyl)-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate 
• 72155-47-6 N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester 
• 1161-13-3 N-Cbz-L-Phe 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 32150-91-7 phthaloyl-L-phenylalanyl chloride 
• 5123-55-7 Nα-phthaloyl-L-phenylalanine 
• 55722-86-6 (2S)-1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanal 
• 178680-13-2 [(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid methyl ester 
• 162221-28-5 4-Nitro-benzenesulfonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester 
• 161525-75-3 (2S,3S)-2-hydroxy-3-phthalimido-4-phenylbutyronitrile 
• 176972-61-5 (S)-(1-benzyl-3-chloro-2-oxopropyl)carbamic acid methyl ester 

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 articles and documents

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

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.