158895-85-3

Upstream product

• 72155-47-6 N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester 
• 112271-08-6 (4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 158744-40-2 Ethyl 4(S)-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate 

Downstream Products

• 178113-55-8 (4S,5R)-4-Benzyl-5-[(R)-1-((S)-1-benzyloxycarbonyl-ethyl)-octyloxycarbonylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 136522-18-4 2-<3(S)-<amino>-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 
• 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 
• 142580-65-2 [(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester 
• 136630-89-2 (4S,5S)-4-benzyl-5-(bromomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine 
• 136630-87-0 (2S,3S)-1-bromo-3-<(tert-butoxycarbonyl)amino>-4-phenyl-2-butanol 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 178113-57-0 (4S,5R)-5-{(R)-1-[(S)-1-((S)-1-Allyloxycarbonyl-2-methyl-propoxycarbonyl)-ethyl]-octyloxycarbonylmethyl}-4-benzyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 178113-58-1 (4S,5R)-4-Benzyl-5-{(R)-1-[(S)-1-((S)-1-carboxy-2-methyl-propoxycarbonyl)-ethyl]-octyloxycarbonylmethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 178113-60-5 (2S,5S,6R,10R,11S)-5-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10-heptyl-2-isopropyl-11-methyl-1,9-dioxa-4-aza-cyclododecane-3,8,12-trione 
• 178113-59-2 N-desmethylhapalosin 
• 159542-04-8 (-)-hapalosin 

Relevant academic research and scientific papers

Chemical study on hapalosin, a cyclic depsipeptide possessing multidrug resistance reversing activities: Synthesis, structure and biological activity

Hapalosin 1 possessing a multidrug resistance reversing activity, has been synthesized from the corresponding hydroxy acids A, C and γ-amino acid B. The stereochemistry of the natural product 1 and N-demethylhapalosin 11 is discussed by means of spectroscopic manner as well as molecular modeling studies. Biological evaluation of 1 and 11 indicated that a cis-amide function is a crucial factor for the MDR reversing activity.

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.