158744-39-9

Basic information

• Product Name: Ethyl 4(S)-benzyl-3-(benzyloxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate
• Synonyms: Ethyl 4(S)-benzyl-3-(benzyloxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate
• CAS NO: 158744-39-9
• Molecular Weight: 411.498
• Mol File: 158744-39-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Ethyl 4(S)-benzyl-3-(benzyloxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4(S)-benzyl-3-(benzyloxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate(158744-39-9)
• EPA Substance Registry System: Ethyl 4(S)-benzyl-3-(benzyloxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate(158744-39-9)

Safety Data

• Hazardous Substances Data: 158744-39-9(Hazardous Substances Data)

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 158744-37-7 Ethyl 4(S)-(benzyloxyformamido)-3(R)-hydroxy-5-phenylpentanoate 
• 1161-13-3 N-Cbz-L-Phe 

Downstream Products

• 136522-18-4 2-<3(S)-<amino>-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 137431-05-1 2-<3(S)-(Benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(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 
• 1027376-26-6 4(S)-Benzyl-3-(benzyloxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid chloride 
• 120452-06-4 3(S)-(Benzyloxyformamido)-1-bromo-4-phenyl-2(S)-butanol 
• 198020-19-8 (2R,2S)-(3S)-1,2-epoxy-3-phenylmethoxycarbonylamino-4-phenylbutane 
• 136522-17-3 cis-N-butyldecahydro-2-<2(R)-hydroxy-4-phenyl-3(S)-aminobutyl>-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 127779-20-8 Saquinavir 
• 158744-41-3 4(S)-Benzyl-3-(benzyloxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid 

Relevant articles and documents

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.