5680-86-4

Usage

Chemical Properties

White crystalline powder

Uses

N-Benzyloxycarbonyl-L-glutamic acid 5-benzyl ester is used as pharmaceutical intermediates.

InChI:InChI=1/C20H21NO6/c22-18(26-13-15-7-3-1-4-8-15)12-11-17(19(23)24)21-20(25)27-14-16-9-5-2-6-10-16/h1-10,17H,11-14H2,(H,21,25)(H,23,24)/t17-/m0/s1

Upstream product

• 56-86-0 L-glutamic acid 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 1676-73-9 L-glutamic acid γ-benzyl ester 
• 100-51-6 benzyl alcohol 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 5894-89-3 γ-benzyl α-(4-nitrophenyl) benzyloxycarbonyl-L-glutamate 
• 122701-22-8 N⁶-(O-benzyl-N-benzyloxycarbonyl-L-α-glutamyl)-N²-(toluene-4-sulfonyl)-L-lysine benzyl ester 
• 34312-72-6 N-(O-benzyl-N-benzyloxycarbonyl-L-α-glutamyl)-L-tyrosine benzyl ester 
• 139937-97-6 Z-L-isoGln-OBzl 
• 108039-06-1 O-benzyl-N-benzyloxycarbonyl-α-glutamyl=>tyrosyl=>tyrosyl=>tyrosine ethyl ester 
• 7540-08-1 benzyloxycarbonyl-γ-benzyl-α-L-glutamyl-D-glutamic acid dibenzyl ester 
• 6922-66-3 benzyloxycarbonyl-γ-benzyl-α-L-glutamyl-L-glutamic acid dibenzyl ester 
• 96467-84-4 N-(O-benzyl-N-benzyloxycarbonyl-L-α-glutamyl)-D-alanine benzyl ester 
• 96467-84-4 N-(O-benzyl-N-benzyloxycarbonyl-L-α-glutamyl)-L-alanine benzyl ester 
• 3190-71-4 5-benzyl L-glutamate N-carboxyanhydride 
• 124290-67-1 N⁶-(O-benzyl-N-benzyloxycarbonyl-L-α-glutamyl)-N²-[N-(toluene-4-sulfonyl)-glycyl]-L-lysine benzyl ester 
• 6402-94-4 (S)-4-Benzyloxycarbonylamino-4-((S)-1-carboxy-2-hydroxy-ethylcarbamoyl)-butyric acid benzyl ester 
• 105975-54-0 Z-α-Glu-(γ-benzylester)-(N^δ,Z)-Orn-(benzylester) 
• 106066-16-4 Cbo-L-Gly-(γ-benzylester)-nitro-L-Arg-methylester 

Relevant academic research and scientific papers

Preparation method of N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid

The invention provides a preparation method of N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid. The preparation method mainly solves the technical problems of complexity, long period, high cost, and low yield of an original process, and comprises the following steps: (1) preparing N-fluorenylmethoxycarbonyl-L-glutamic acid; (2) preparing N-fluorenylmethoxycarbonyl-L-glutamic acid-1-benzyl ester; (3) preparing S-triphenylmethyl cysteamine; (4) preparing N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid-alpha-benzyl ester; and (5) preparing N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid. The method is rapid, high in yield and simple in separation and purification, and the used solvent is environment-friendly and is suitable for mass production.

Asymmetric michael addition of malonates to enones catalyzed by a primary Β-amino acid and its lithium salt

Highly enantioselective Michael addition of malonates to enones was achieved using a mixed catalyst consisting of a primary Β-amino acid, O-TBDPS (S)-Β-homoserine, and its lithium salt. Various cyclic and acyclic enones were converted into 1,5-ketoesters in high yields (up to 92%) with high enantioselectivity (up to 97% ee) under mild reaction conditions. Details of synthesis of the catalyst, optimization of the reaction conditions for the Michael addition reaction, and a plausible reaction mechanism are described.

Glutamyl adenylate analogues are inhibitors of glutamyl-tRNA synthetase

Glutamol adenylate 10 was a competitive inhibitor (K(i) = 3 μM) of glutamyl-tRNA synthetase from Escherichia coli. The N6-benzoyl adenine derivative 9 was also an inhibitor (K(i) ~ 60 μM). Replacement of adenine by other bases (purine, cytosine

Selective removal of phenacyl ester group with a TBAF·xH2O-thiol system from amino acid derivatives containing benzyl or 4-nitrobenzyl ester

A facile cleavage method of phenacyl ester bonds by combined use of tetrabutylammonium fluoride hydrate (TRAF·xH2O) and 1-octanethiol was established. Benzyl and 4-nitrobenzyl esters are almost stable toward this reagent.