510713-99-2

Upstream product

• 510713-90-3 (R)-benzyl 4-(1-(1H-imidazole-1(R/S)-carbonothioyloxy)-3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 510713-88-9 (4R)-4-[(1RS)-2-ethoxycarbonyl-2,2-difluoro1-hydroxyethyl]-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester 
• 357958-50-0 N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester 
• 133464-35-4 3-benzyl 4-methyl (4R)-2,2-dimethyloxazolidine-3,4-dicarboxylate 
• 133464-36-5 (S)-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester 
• 501-53-1 benzyl chloroformate 
• 133464-37-6 (4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester 
• 34897-61-5 N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt 
• 93204-36-5 (R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate 
• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 510713-97-0 H-Glu(α-OtBu)(γ-OTMSE) 
• 510713-92-5 (4S)-4-(2-ethoxycarbonyl-2,2-difluoroethyl)-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester 

Downstream Products

• 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 
• 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 academic research and scientific papers

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.