5211-24-5

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

• 84062-30-6 methyl 1-benzyloxycarbonyl-(4S)-phenylseleno-(2S)-pyrrolidinylcarboxylate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 186145-08-4 (2S)-2,5-dihydro-1H-pyrrole-2-carboxylate hydrochloride 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 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 
• 51-35-4 4R-4-hydroxyproline 
• 501-53-1 benzyl chloroformate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 

Downstream Products

• 111193-60-3 (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline methyl ester 
• 175735-53-2 (2S,3R,4S)-(N-Benzyloxycarbonyl)-6,6-dicarboxy-3,4-methano-L-proline trimethyl 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 
• 886447-82-1 ethyl [4-[N-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate 
• 317354-96-4 ethyl [4-[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate 
• 317358-60-4 [4-((2S,3R,4S)-3,4-Dihydroxy-1-{2-[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-pyrrolidine-2-carbonyl)-piperazin-1-yl]-acetic acid ethyl ester 
• 111193-62-5 (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester 
• 111193-64-7 methyl 1-benzyloxycarbonyl-(3S,4R)-isopropylidenedioxy-(2S)-pyrrolidinylcarboxylate 
• 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 

Relevant academic research and scientific papers

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.

First total synthesis of penmacric acid and its stereoisomer

The total synthesis of penmacric acid and its stereoisomer, epipenmacric acid, is reported for the first time starting from trans-4-hydroxy-l-proline. Et3B-induced diastereoselective radical addition reaction was used to control stereoselectivity at the C3 stereogenic center as a key step.

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).

BIOLOGICALLY ACTIVE COMPOUNDS

Compounds of general formula (I) wherein: Z = CR3R4, where R3 and R4 are independently chosen from CO-7-alkyl P1 = CR5R6, P2 = O, CR7R8/sup

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

The preparation of (S)-3,4-dehydroproline from (2S,4R)-4-hydroxyproline

(2S,4R)-N-benzyloxycarbonyl-4-tosyloxyproline methyl ester, readily prepared from commercially available (2S,4R)-N-benzyloxycarbonyl-4-hydroxyproline, was converted to (S)-3,4-dehydroproline of high enantiomeric purity by a process which involved a highly regioselective phenylselenoxide elimination to introduce the olefinic function.