153080-92-3

Basic information

• Product Name: ethyl (2S,4S)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate
• Synonyms: ethyl (2S,4S)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate
• CAS NO: 153080-92-3
• Molecular Weight: 347.411
• Mol File: 153080-92-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: ethyl (2S,4S)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (2S,4S)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate(153080-92-3)
• EPA Substance Registry System: ethyl (2S,4S)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate(153080-92-3)

Safety Data

• Hazardous Substances Data: 153080-92-3(Hazardous Substances Data)

Upstream product

• 153080-85-4 ethyl (2S,4R)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate 
• 171038-44-1 (S)-5-Oxo-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 100-39-0 benzyl bromide 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 100-52-7 benzaldehyde 

Downstream Products

• 170947-82-7 ethyl (2S,4S)-N-BOC-4-benzylprolinate 
• 129446-71-5 (2S,4S)-2-Amino-4-benzyl-pentanedioic acid 
• 166757-32-0 Ethyl (2S,4S,5R)-4-benzyl-5-butylprolinate 
• 129446-70-4 (2S,4R)-2-amino-4-benzyl pentanedioic acid 

Relevant articles and documents

4-Substituted D-glutamic acid analogues: The first potent inhibitors of glutamate racemase (MurI) enzyme with antibacterial activity

The first potent inhibitors of glutamate racemase (MurI) enzyme that show whole cell antibacterial activity are described. Optically pure 4-substituted D-glutamic acid analogues with (2R,4S) stereochemistry and bearing aryl-, heteroaryl-, cinnamyl-, or biaryl-methyl substituents represent a novel class of glutamate racemase inhibitors. Exploration of the D-Glu core led to the identification of lead compounds (-)-8 and 10. 2-Naphthylmethyl derivative 10 was found to be a potent competitive inhibitor of glutamate racemase activity (Ki = 16 nM, circular dichroism assay; IC50 = 0.1 μg/mL high-performance liquid chromatography (HPLC) assay). Thorough structure-activity relationship (SAR) studies led to benzothienyl derivatives such as 69 and 74 with increased potency (IC50 = 0.036 and 0.01 μg/mL, respectively, HPLC assay). These compounds showed potent whole cell antibacterial activity against S. pneumoniae PN-R6, and good correlation with the enzyme assay. Compounds 69, 74 and biaryl derivative 52 showed efficacy in an in vivo murine thigh infection model against Streptococcus pneumoniae. Data described herein suggest that glutamate racemase may be a viable target for developing new antibacterial agents.

New enantioselective approach to α-allokainoids by Michael addition to chiral 4-substituted 2,3-didehydroprolinate

(-) and (+) α-Allokainoids hydrochlorides 3 and 4 were obtained by hydrolysis of the corresponding Michael adducts resulting from the addition of diethyl malonate to chiral N-urethane protected ethyl 4-benzyl-2,3-didehydroprolinates 9 and 13 respectively.

Stereoselective Reactions of Lithium Enolates Derived from N-BOC Protected Pyroglutamic Esters

The lithium enolates of N-Boc protected pyroglutamic ethyl or tert-butyl esters react with electrophiles in good yield without epimerization of the chiral centre.With benzyl bromides the process is stereospecific, yielding exclusively the trans isomer.However, with other reactive electrophiles a 2:1 tans/cis diastereometric mixture was obtained, regardless of the steric bulk of the ester group.