94885-52-6

Basic information

• Product Name: L-Proline, 5-oxo-, phenylmethyl ester
• CAS NO: 94885-52-6
• Molecular Formula: C12H13NO3
• Molecular Weight: 219.24
• Mol File: 94885-52-6.mol
• Article Data: 23

Chemical Properties

• CAS DataBase Reference: L-Proline, 5-oxo-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 5-oxo-, phenylmethyl ester(94885-52-6)
• EPA Substance Registry System: L-Proline, 5-oxo-, phenylmethyl ester(94885-52-6)

Safety Data

• Hazardous Substances Data: 94885-52-6(Hazardous Substances Data)

Usage

General Description

L-Proline, 5-oxo-, phenylmethyl ester, also known as phenylmethyl L-proline, is a chemical compound with the molecular formula C12H13NO3. It is a derivative of the amino acid L-proline and is commonly used as a building block in the synthesis of various pharmaceuticals and biologically active compounds. Its phenylmethyl ester group makes it more stable and suitable for use in organic chemistry reactions. L-Proline, 5-oxo-, phenylmethyl ester has applications in drug development, as well as in the production of peptides and peptide-based drugs. It is important for its role as a chemical intermediate in the pharmaceutical industry.

Upstream product

• 60555-57-9 benzyl 5-oxopyrrolidine-2-carboxylate 
• 1468-39-9 Isovaleric anhydride 
• 18087-65-5 1-Benzyl-4,5-dichlor-1H-pyrrol-2-carbonsaeure-methylester 
• 103301-78-6 1-benzyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 100-39-0 benzyl bromide 
• 98-79-3 L-Pyroglutamic acid 
• 71389-33-8 dibenzyl (2S)-5-oxotetrahydro-1H-pyrrole-1,2-dicarboxylate 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 

Downstream Products

• 105424-85-9 benzyl N-acetyl-(L)-pyroglutamate 
• 504438-61-3 Boc-L-Val-L-pGlu-OBn 
• 454228-40-1 Boc-(L-pGlu)4-OBzl 
• 454228-37-6 Boc-(L-pGlu)3-OBzl 
• 454228-34-3 Boc-(L-pGlu)2-OBzl 
• 363139-40-6 Boc-L-Ala-L-pGlu-OBn 
• 202918-12-5 (S)-1-(tert-Butyl-dimethyl-silanyl)-5-oxo-pyrrolidine-2-carboxylic acid benzyl ester 
• 71389-33-8 dibenzyl (2S)-5-oxotetrahydro-1H-pyrrole-1,2-dicarboxylate 
• 146356-00-5 N-methoxycarbonyl (S)-pyroglutamic acid benzylester 
• 90891-25-1 -(S)-alanyl>-(S)-pyroglutamic acid benzyl ester 
• 90940-58-2 -(R)-alanyl>-(S)-pyroglutamic acid benzyl ester 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 
• 106116-09-0 L-5-Oxo-1-(trimethylsilyl)prolin-benzylester 

Relevant articles and documents

Enantiopure 5-CF3-Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry

The straightforward synthesis of enantiopure 5-(R)-and 5-(S)-trifluoromethylproline is reported. The key steps are a Ruppert-Prakash reagent addition on l-pyroglutamic esters followed by an elimination reaction and a selective reduction. The solution-phase and solid-phase incorporation of this unprotected enantiopure fluorinated amino acid in a short peptide chain was demonstrated. Compared to proline, the CF3 group provides a decrease of the trans to cis amide bond isomerization energy and an increase of the cis conformer population.

Synthesis of the Siderophore Coelichelin and Its Utility as a Probe in the Study of Bacterial Metal Sensing and Response

A convergent total synthesis of the siderophore coelichelin is described. The synthetic route also provided access to acetyl coelichelin and other congeners of the parent siderophore. The synthetic products were evaluated for their ability to bind ferric iron and promote growth of a siderophore-deficient strain of the Gram-negative bacterium Pseudomonas aeruginosa under iron restriction conditions. The results of these studies indicate coelichelin and several derivatives serve as ferric iron delivery vehicles for P. aeruginosa.

A new class of non-C2-symmetric ligands for oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones

We report the discovery, synthesis, and application of a new class of non-C2-symmetric phosphoramidite ligands derived from pyroglutamic acid for use in both oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones. The resulting chiral products are typically obtained in high yield with good to excellent levels of enantioselectivity.