71389-33-8

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-, bis(phenylMethyl) ester, (S)-
• Synonyms: 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-, bis(phenylMethyl) ester, (S)-
• CAS NO: 71389-33-8
• Molecular Weight: 353.375
• Mol File: 71389-33-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-, bis(phenylMethyl) ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-, bis(phenylMethyl) ester, (S)-(71389-33-8)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-, bis(phenylMethyl) ester, (S)-(71389-33-8)

Safety Data

• Hazardous Substances Data: 71389-33-8(Hazardous Substances Data)

Usage

Chemical compound

1,2-Pyrrolidinedicarboxylic acid, 5-oxo-, bis(phenylMethyl) ester, (S)-

Usage

Synthesis of pharmaceuticals
Protecting group for amines in organic chemistry

Physical state

White solid

Molecular weight

341.4 g/mol

Chirality

(S)enantiomer is more commonly used

Role

Stereoselective synthesis of chiral compounds

Safety precautions

Causes irritation to eyes, skin, and respiratory system
Proper safety measures should be followed when working with it

Upstream product

• 3705-42-8 Cbz-(L)-Glu-OBn 
• 32159-21-0 Cbz-L-pGlu-OH 
• 100-44-7 benzyl chloride 
• 700-57-2 1-adamantanol 
• 4561-10-8 L-glutamic acid dibenzyl ester hydrochloride 
• 501-53-1 benzyl chloroformate 
• 53363-74-9 N-Z-L-Glu-OBzl-γ-Dcha salt 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 881883-91-6 Z-Glutaminsaeure-α-benzylester-γ-chlorid 
• 94885-52-6 benzyl (L)-pyroglutamate 
• 100-39-0 benzyl bromide 
• 538-75-0 dicyclohexyl-carbodiimide 

Downstream Products

• 245648-24-2 (5S,2'S,5'S)-[1'-benzyloxycarbonyl-5'-carboxybenzyl-2'-pyrrolidinyl]-5-methylfuran-2(5H)-one 
• 245648-25-3 (5R,2'S,5'S)-[1'-benzyloxycarbonyl-5'-carboxybenzyl-2'-pyrrolidinyl]-5-methylfuran-2(5H)-one 
• 134038-65-6 (S)-2-Benzyloxycarbonylamino-3-[5-hydroxy-1-(4-nitro-phenyl)-1H-pyrazol-4-yl]-propionic acid benzyl ester 
• 191790-37-1 benzyl (2S,4RS)-1-benzyloxycarbonyl-4-(2,4-dinitrophenyl)hydrazonomethylpyroglutamate 
• 134038-68-9 benzyl (2S)-2-benzyloxycarbonylamino-3-<2-acetyl-1-(p-nitrophenyl)-5-oxopyrazol-4-yl>propionate 
• 191790-24-6 benzyl (2S,4RS)-1-benzyloxycarbonyl-4-(p-nitrophenyl)-hydrazonomethylpyroglutamate 
• 134038-64-5 benzyl (2S)-2-benzyloxycarbonylamino-3-(5-hydroxy-1-phenyl-pyrazol-4-yl)propionate 
• 134038-67-8 benzyl (2S)-2-benzyloxycarbonylamino-3-(2-acetyl-1-methyl-5-oxopyrazol-4-yl)propionate 
• 134038-62-3 benzyl (2S)-2-benzyloxycarbonylamino-3-(1-methyl-5-hydroxypyrazol-4-yl)propionate 
• 134038-59-8 (S)-4-Formyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 
• 245648-23-1 (S)-5-Hydroxy-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 
• 94885-52-6 benzyl (L)-pyroglutamate 
• 134174-76-8 benzyl (2S)-1-benzyloxycarbonyl-4-dimethylaminomethylenepyroglutamate 
• 127949-80-8 benzyl (2S)-1-benzyloxycarbonyl-4-(hydroxyphenylmethyl)pyroglutamate 

Relevant articles and documents

Green preparation method of N-substituted-L-pyroglutamate

The invention provides a green preparation method of N-substituted-L-pyroglutamate. The method comprises the steps as follows: L-glutamic acid diester hydrochloride (III) is prepared from L-glutamic acid (II) as a starting material in the presence of an acidic reagent by an esterification reaction; then, L-glutamic acid diester hydrochloride (III) is subjected to N-substituted protective reactionwith an N-substituent protective reagent with a one-pot method in the presence of a base and a solvent, an N-substituted protective group is introduced, heating is performed for dealcoholization cyclization in molecules, and N-substituted-L-pyroglutamate as shown in the formula (I) is obtained. The method has the advantages of cheap and easily available raw materials, classic reaction types, shortprocess route, simple and convenient operation, small waste water amount, green and environment-friendly production process, high reaction yield and low product cost. 5R-benzyloxyaminopiperidine-2S-carboxylate, 5R-benzyloxyaminopiperidine-2S-formate ethanedioate and avibactam can be prepared from N-substituted-L-pyroglutamate as shown in the formula (I).

Synthesis of Two Stable Nitrogen Analogues of S-Adenosyl-L-methionine

Homochiral syntheses of two stable nitrogen analogues of S-adenosyl-L-methionine (AdoMet) are described. In the first analogue, AzaAdoMet, the sulfonium center of AdoMet, is replaced by an N-methyl moiety whose pKa is 7.08. This provides a char

Stereospecific synthesis of (2S,4R)-[5,5,5-2H3]leucine

The first stereospecific chemical synthesis of a sample of the amino acid (2S)-leucine labelled in one of the diastereotopic methyl groups has been achieved using (2S)-pyroglutamic acid as a chiral template. This has been used to develop a method for assigning resonances to the diastereotopic methyl groups of the leucine residues in the 1H NMR spectra of proteins.