421556-71-0

Basic information

• Product Name: (S)-4-[7-{2-Benzyloxy-5-[(S)-2-benzyloxycarbonylamino-2-((S)-1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-2-oxo-1,2-dihydro-indol-(3E)-ylidenemethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• Synonyms: (S)-4-[7-{2-Benzyloxy-5-[(S)-2-benzyloxycarbonylamino-2-((S)-1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-2-oxo-1,2-dihydro-indol-(3E)-ylidenemethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS NO: 421556-71-0
• Molecular Weight: 918.056
• Mol File: 421556-71-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (S)-4-[7-{2-Benzyloxy-5-[(S)-2-benzyloxycarbonylamino-2-((S)-1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-2-oxo-1,2-dihydro-indol-(3E)-ylidenemethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-[7-{2-Benzyloxy-5-[(S)-2-benzyloxycarbonylamino-2-((S)-1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-2-oxo-1,2-dihydro-indol-(3E)-ylidenemethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester(421556-71-0)
• EPA Substance Registry System: (S)-4-[7-{2-Benzyloxy-5-[(S)-2-benzyloxycarbonylamino-2-((S)-1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-2-oxo-1,2-dihydro-indol-(3E)-ylidenemethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester(421556-71-0)

Safety Data

• Hazardous Substances Data: 421556-71-0(Hazardous Substances Data)

Upstream product

• 1080-06-4 L-Tyr-OMe 
• 13512-31-7 N-(benzyloxycarbonyl)-L-tyrosine methyl ester 
• 119140-66-8 N-Cbz-O-benzyl-L-tyrosine methyl ester 
• 421556-70-9 (S)-4-[7-[2-Benzyloxy-5-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-phenyl]-2-oxo-1,2-dihydro-indol-(3E)-ylidenemethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 421556-69-6 (S)-N-benzyloxycarbonyl-3-(4-benzyloxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester 
• 421556-68-5 (S)-N-benzyloxycarbonyl-3-(4-benzyloxy-3-iodophenyl)alanine methyl ester 
• 421556-67-4 4-(7-iodo-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 421556-66-3 4-(7-iodo-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 
• 60-18-4 L-tyrosine 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 
• 615-43-0 2-iodophenylamine 
• 31676-49-0 7-iodooxindole 
• 20780-78-3 7-iodoisatin 

Downstream Products

• 262854-05-7 TMC-95A 
• 421556-73-2 2-(3-{4-benzyloxy-3-[3-(2-tert-butoxycarbonylamino-1,3-dihydroxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid tert-butyl ester 
• 421556-74-3 2-(3-{4-benzyloxy-3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid tert-butyl ester 
• 262854-05-7 TMC-95B 
• 421556-72-1 4-[(7-{2-benzyloxy-5-[2-benzyloxycarbonylamino-2-(1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant articles and documents

Total synthesis of TMC-95A and -B via a new reaction leading to Z-enamides. Some preliminary findings as to SAR

A full account of the total syntheses of proteasome inhibitors TMC-95A and -B is provided. A key feature of the syntheses involved installation of a cis-propenylamide moiety by a thermal rearrangement of an α-silylallyl amide. The scope and mechanism of the enamide-forming reaction are discussed. Also provided are some preliminary results from SAR studies. It was found that simplified analogues can retain the full potency of proteasome inhibition.