357958-50-0

Basic information

• Product Name: N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester
• Synonyms: N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester
• CAS NO: 357958-50-0
• Molecular Weight: 437.608
• Mol File: 357958-50-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester(357958-50-0)
• EPA Substance Registry System: N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester(357958-50-0)

Safety Data

• Hazardous Substances Data: 357958-50-0(Hazardous Substances Data)

Upstream product

• 203919-89-5 (S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic acid benzyl ester 
• 23632-67-9 (S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid 
• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 34897-61-5 N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt 
• 115-11-7 isobutene 
• 1006729-24-3 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-(2-trimethylsilanyl-ethyl) ester 

Downstream Products

• 357958-48-6 (S)-4-[(S)-1-Carboxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-2-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyric acid 
• 357958-53-3 Z-Glu(α-OtBu)-γ-Glu(α-OtBu)(γ-OTMSE) 
• 5891-45-2 (S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester 
• 510714-05-3 2-(2-tert-butoxycarbonylamino-benzoylamino)-4-{1-tert-butoxycarbonyl-3-[1-tert-butoxycarbonyl-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-4,4-difluoro-butyric acid tert-butyl ester 
• 510714-03-1 N-Boc-Abz-4,4-difluoroglutamic acid α-tert-butyl ester γ-glutamic acid α-tert-butyl γ-2-(trimethylsilyl)ethyl ester 
• 510714-09-7 N-Cbz-(2S)-4,4-difluoroglutamic acid α-tert-butyl ester γ-glutamic acid α-tert-butyl γ-2-(trimethylsilyl)ethyl ester 
• 510713-99-2 N-Cbz-difluorooxazolidine-γ-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester 
• 510714-01-9 (S)-2-((S)-4-Benzyloxycarbonylamino-2,2-difluoro-5-hydroxy-pentanoylamino)-pentanedioic acid 1-tert-butyl ester 5-(2-trimethylsilanyl-ethyl) ester 

Relevant articles and documents

The synthesis of (2S)-4,4-difluoroglutamyl γ-peptides based on Garner's aldehyde and fluoro-reformatsky chemistry

The development of optically active fluorinated synthetic building blocks of general utility is a current goal of organo-fluorine chemists. The serine-derived Garner aldehyde was converted to a general 4,4-difluoroamino acid building block via fluoro-Reformatsky reaction with ethyl bromodifluoroacetate. The utility of this building block was demonstrated by the synthesis of derivatives of (2S)-4,4-difluoroglutamine, (2S)-4,4-difluoroglutamic acid, and its incorporation into a fluorophore-containing isopeptide 2 designed as a mechanistic probe of γ-glutamyl hydrolase. Compound 2 proved to be a substrate for γ-glutamyl hydrolase and was hydrolyzed at a rate significantly slower than the corresponding non-fluorinated analog.