5211-24-5

Basic information

• Product Name: 1H-Pyrrole-1,2-dicarboxylic acid, 2,5-dihydro-, 2-methyl 1-(phenylmethyl) ester, (2S)-
• CAS NO: 5211-24-5
• Molecular Formula: C14H15NO4
• Molecular Weight: 261.277
• Mol File: 5211-24-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole-1,2-dicarboxylic acid, 2,5-dihydro-, 2-methyl 1-(phenylmethyl) ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-1,2-dicarboxylic acid, 2,5-dihydro-, 2-methyl 1-(phenylmethyl) ester, (2S)-(5211-24-5)
• EPA Substance Registry System: 1H-Pyrrole-1,2-dicarboxylic acid, 2,5-dihydro-, 2-methyl 1-(phenylmethyl) ester, (2S)-(5211-24-5)

Safety Data

• Hazardous Substances Data: 5211-24-5(Hazardous Substances Data)

Usage

Molecular weight

257.27 g/mol The molecular weight is the mass of a molecule, typically expressed in grams per mole (g/mol). It is calculated by adding the atomic weights of all the atoms in the molecule.

Ester derivative

The compound is an ester derivative of pyrrole-1,2-dicarboxylic acid, which means it has an ester functional group (-COO-) attached to the pyrrole ring.

Pyrrole ring

The compound contains a pyrrole ring, which is a five-membered aromatic ring with one nitrogen atom and four carbon atoms.

Two carboxylic acid groups

The compound has two carboxylic acid groups (-COOH) attached to the pyrrole ring, which are located at the 1 and 2 positions.

Methyl group

The compound has a methyl group (-CH3) attached to the 2 position of the pyrrole ring.

(2S)configuration

The stereochemistry at the second carbon of the pyrrole ring is in the S configuration, which means that the two substituents attached to that carbon are in a clockwise orientation when viewed from the top.

Pharmaceutical and research applications

The compound is commonly used as a building block in the synthesis of various compounds in pharmaceutical and research applications.

Upstream product

• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 186145-08-4 (2S)-2,5-dihydro-1H-pyrrole-2-carboxylate hydrochloride 
• 928065-03-6 (2S,4S)-4-iodo-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester 
• 57653-38-0 N-<(phenylmethoxy)carbonyl>-4(R)-<<(4-methylphenyl)sulfonyl>oxy>-(S)-proline methyl ester 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 501-53-1 benzyl chloroformate 
• 84062-30-6 methyl 1-benzyloxycarbonyl-(4S)-phenylseleno-(2S)-pyrrolidinylcarboxylate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 

Downstream Products

• 111193-60-3 (S)-3,4-Dihydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 4043-88-3 3,4-dehydro-L-proline 
• 648934-18-3 (S)-2-hydroxymethyl-2,5-dihydropyrrole-1-carboxylic acid benzyl ester 
• 928065-04-7 (1R,2S,5S)-6-oxa-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-methyl 3-(phenylmethyl) ester 
• 928065-02-5 (2S,3R,4R)-3-hydroxy-4-iodo-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenyl methyl) ester 
• 928065-01-4 (2S,3S,4S)-3-hydroxy-4-[2-methoxy-2-oxo-1-[(phenylmethoxy)amino]ethyl]-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester 
• 111193-66-9 (3aR,4R,6aS)-2,2-Dimethyl-4-(toluene-4-sulfonyloxymethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 
• 111193-67-0 (3aR,4S,6aS)-4-((S)-3-Amino-3-carboxy-propylsulfanylmethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 
• 111193-68-1 (3aR,4S,6aS)-2,2-Dimethyl-4-methylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 
• 111265-96-4 (2R,3R,4S)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol 3,4-O-isopropylidene acetal 
• 159262-32-5 (2S,3R,4S,6S) 6-Carboxy-3,4-methanoproline 
• 159262-32-5 (2S,3R,4S,6R) 6-Carboxy-3,4-methanoproline 
• 648934-49-0 (3aR,6S,6aS)-1-[(2S)-2-(4-tert-butylbenzoylamino)-4-methylpentanoyl]-6-hydroxyhexahydropyrrolo[3,2-c]pyrazole-2,4-dicarboxylic acid 4-benzyl ester 2-tert-butyl ester 
• 648934-51-4 (3aR,6S,6aS)-4-benzoyl-1-[(2S)-2-(4-tert-butylbenzoylamino)-4-methylpentanoyl]-6-hydroxyhexahydropyrrolo[3,2-c]pyrazole-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

Total synthesis of penmacric acids via an intermolecular radical addition reaction

The total syntheses of penmacric acid and its three stereoisomers were accomplished through the intermolecular radical addition reaction of the 4-pyrrolidyl radical derived from trans-4-hydroxy-l-proline. Furthermore, 1′,3-diepi-penmacric acid was synthesized stereoselectively via double stereoinduction in the radical reaction.

Synthesis, biological evaluation, and pharmacokinetic study of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives as VLA-4 antagonists

A series of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives were synthesized and evaluated for their activity as VLA-4 antagonists. Of 22 compounds synthesized, 19 compounds showed potent activity with low nanomolar IC50 values. In addition, the representative compounds 11o and 11p with a hydroxy group in the pyrrolidine ring showed moderate plasma clearance in rats (11o, 30 ml/min/kg and 11p, 21 ml/min/kg) and in dogs (11o, 12 ml/min/kg and 11p, 9 ml/min/kg).

Synthesis of (2R,3R,4S)-2-hydroxymethylpyrrolidine-3,4-diol from (2S)-3,4-dehydroproline derivatives

(2R,3R,4S)-2-Hydroxymethylpyrrolidine-3,4-diol (1,4-dideoxy-1,4-imino-D-ribitol) was synthesized in five steps from N-protected (2S)-3,4-dehydroproline methyl esters.The stereoselective reaction of osmium tetraoxide with dehydroproline derivatives gave hi