102572-59-8

Upstream product

• 868-72-4 dimethyl (2R,5S)-2,5-dibromohexanedioate 
• 102508-03-2 cis-2,5-dimethyl N-benzylpyrrolidine-2,5-dicarboxylate 
• 124-04-9 Adipic acid 
• 111-50-2 Adipic acid dichloride 
• 100-46-9 benzylamine 

Downstream Products

• 113304-86-2 (2R,5S)-1-Benzyl-5-hydroxymethyl-pyrrolidine-2-carboxylic acid methyl ester 
• 172885-61-9 (2R,5S)-1-Benzyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-2-carbaldehyde 
• 173006-72-9 [(2R,5S)-1-Benzyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-2-yl]-methanol 
• 172885-55-1 [(2R,5S)-1-Benzyl-5-(tetrahydro-pyran-2-yloxymethyl)-pyrrolidin-2-yl]-methanol 
• 172885-66-4 (2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 172885-67-5 (2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 172885-77-7 (2S,5R)-2-Hydroxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 1025827-74-0 (2R,5S)-1-Benzyl-5-(tetrahydro-pyran-2-yloxymethyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 172885-71-1 (2R,5S)-2-(Dimethoxy-phosphorylmethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 172885-64-2 [(2R,5S)-1-Benzyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-2-ylmethyl]-phosphonic acid dimethyl ester 
• 172885-56-2 (2R,5S)-2-Hydroxymethyl-5-(tetrahydro-pyran-2-yloxymethyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 172885-70-0 (2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(dimethoxy-phosphorylmethyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 172885-58-4 (2R,5S)-2-Methanesulfonyloxymethyl-5-(tetrahydro-pyran-2-yloxymethyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 172885-72-2 Pentanedioic acid mono-[(2S,5R)-1-benzyloxycarbonyl-5-(dimethoxy-phosphorylmethyl)-pyrrolidin-2-ylmethyl] ester 

Relevant academic research and scientific papers

Enzymatic desymmetrization of pyrrolidine and pyrroline derivatives

The enzymatic desymmetrization of various meso-N-Boc-2,5-cis-disubstituted pyrrolidines and pyrrolines compounds by ester hydrolysis or transesterification provided the corresponding monoesters in high enantiomeric excess.

Highly Enantioselective Route to (R)-Proline Derivatives via Enzyme Catalysed Hydrolysis of cis-N-Benzyl-2,5-bismethoxycarbonylpyrrolidine in an Aqueous Dimethyl Sulphoxide Medium

Pig liver esterase catalysed hydrolysis of diester (1) with dimethyl sulphoxide as cosolvent in buffered solutions gave optically pure monoester (2) which was further transformed to the (R)-proline related ester (4) by radical decarboxylation.

A mechanochemical approach to access the proline-proline diketopiperazine framework

Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline-proline dipeptides under solvent-free conditions. A deprotection-cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stereoselectivity which could be explained by DFT calculations. Using this method, an enantiopure disubstituted Pro-Pro diketopiperazine was synthesized in 4 steps, making 5 new bonds using a ball mill.

Methyl N-[(2R,5S)-1-N-benzyl-5-methoxycarbonylprolyl]-(S)-phenylalaninate

In order to prepare new chiral auxiliaries useful in developing a new method of synthesis of optically pure amines or β-amino acids, an unsymmetric derivative of pyrrolidine has been obtained, methyl 2-[(2R,5S)-(1-benzyl-5-methoxypyrrolidin-2-yl)carbonyl-(S)-amino]-3- phenylpropanoate, C24H28N2O5. This has been crystallized and subjected to X-ray analysis in order to ascertain the absolute configuration of the two asymmetric C atoms of the ring. The five-membered ring is half-chair shaped. An intramolecular hydrogen bond links the amino N atom of the phenylalanine group to the carbonyl of the 5-methoxycarbonyl group.

DIVERSIFIED SYNTHETIC APPROACHES TO THE CARBAPENEM ANTIBIOTICS BASED ON SYMMETRIZATION-ASYMMETRIZATION CONCEPT

cis-Fused bicyclic β-lactam compound 9, a key intermediate to cis-substituted carbapenem antibiotics, has been synthesized in optically pure form based on symmetrization-asymmetrization concept.