136465-80-0

Basic information

• Product Name: 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane
• Synonyms: 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane
• CAS NO: 136465-80-0
• Molecular Weight: 293.322
• Mol File: 136465-80-0.mol

Chemical Properties

• CAS DataBase Reference: 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane(136465-80-0)
• EPA Substance Registry System: 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane(136465-80-0)

Safety Data

• Hazardous Substances Data: 136465-80-0(Hazardous Substances Data)

Upstream product

• 78571-81-0 (R,R)-3-(phenylmethyl)oxiranemethanol 
• 1055033-80-1 Methanesulfonic acid (1R,2S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-1-(tetrahydro-pyran-2-yloxymethyl)-propyl ester 
• 1054798-68-3 2-[(1S,2R)-1-Benzyl-2-hydroxy-3-(tetrahydro-pyran-2-yloxy)-propyl]-isoindole-1,3-dione 
• 1026632-96-1 2-[(S)-1-Benzyl-2-oxo-3-(tetrahydro-pyran-2-yloxy)-propyl]-isoindole-1,3-dione 
• 32150-91-7 phthaloyl-L-phenylalanyl chloride 
• 5123-55-7 Nα-phthaloyl-L-phenylalanine 
• 136465-82-2 1-Hydroxy-4-phenyl-3(S)-phthalimido-2-butanone 
• 63-91-2 L-phenylalanine 
• 85-44-9 phthalic anhydride 
• 147915-02-4 (2S,3S)-3-amino-4-phenylbutane-1,2-diol 
• 116949-67-8 (2S,3S)-2-azido-1-phenyl-butane-3,4-diol 
• 161525-69-5 (2S,3S)-4-phenyl-3-phthalimidobutane-1,2-diol 
• 136465-83-3 2(R)-(Methanesulfonyloxy)-4-phenyl-3(S)-phthalimido-1-butanol 

Downstream Products

• 127779-20-8 Saquinavir 
• 136522-17-3 cis-N-butyldecahydro-2-<2(R)-hydroxy-4-phenyl-3(S)-aminobutyl>-(4aS,8aS)-isoquinoline-3(S)-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 
• 136522-18-4 2-<3(S)-<amino>-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 136465-78-6 N-tert-Butyldecahydro-2-(2(R)-hydroxy-4-phenyl-3(S)phthalimidobutyl)-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 688349-19-1 2-[(S)-1-((3R,4aR,8aS)-7-Benzyl-1-oxo-6-trimethylsilanyloxy-3,4,4a,5,8,8a-hexahydro-1H-isochromen-3-yl)-2-phenyl-ethyl]-isoindole-1,3-dione 
• 688349-21-5 2-[(S)-1-((3R,4aS,5R,7aS)-5-Benzenesulfonyl-6-methylene-1-oxo-octahydro-cyclopenta[c]pyran-3-yl)-2-phenyl-ethyl]-isoindole-1,3-dione 
• 688349-14-6 (5R,6S)-6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-7-phenyl-hept-2-ynoic acid methyl ester 
• 688349-11-3 2-((1S,2R)-1-Benzyl-2-hydroxy-pent-4-ynyl)-isoindole-1,3-dione 
• 688349-15-7 2-[(S)-1-((R)-6-Oxo-3,6-dihydro-2H-pyran-2-yl)-2-phenyl-ethyl]-isoindole-1,3-dione 
• 207281-59-2 (4R,5S)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenyl-hexanoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 

Relevant articles and documents

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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.