157662-41-4

Basic information

• Product Name: (R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester
• Synonyms: (R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester
• CAS NO: 157662-41-4
• Molecular Weight: 305.331
• Mol File: 157662-41-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester(157662-41-4)
• EPA Substance Registry System: (R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester(157662-41-4)

Safety Data

• Hazardous Substances Data: 157662-41-4(Hazardous Substances Data)

Upstream product

• 121772-98-3 (R)-2-allylpyrrolidine-2-carboxylic acid 
• 129704-91-2 (R)-2-allylpyrrolidine-2-carboxylic acid hydrochloride 
• 157662-40-3 (R)-N-(benzoyloxycarbonyl)-allylproline methyl ester 
• 501-53-1 benzyl chloroformate 
• 121773-05-5 (R)-N-(benzyloxycarbonyl)-2-(2'-propenyl)proline 

Downstream Products

• 325460-76-2 (6R,12S)-1-aza-3-(pyroglutamylamino)-6-[(tert-butyldimethylsiloxy)methyl]-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene 
• 325460-70-6 (6R,12S)-1-aza-3-(pyroglutamylamino)-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene 
• 325460-69-3 (6R,12S)-1-aza-3-(pyroglutamylamino)-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene 
• 325460-77-3 (6R,12S)-1-aza-3-(pyroglutamylamino)-6-formyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene 
• 325460-63-7 (2R)-N-(benzyloxycarbonyl)-2-[2'-(phenyl)-3'-(carbomethoxy)-propyl]proline methyl ester 
• 325460-68-2 (6R)-1-aza-3-amino-6-[(tert-butyldimethylsiloxy)methyl]-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene 
• 325460-67-1 (6R)-1-aza-6-[(tert-butyldimethylsiloxy)methyl]-3-hydroxy-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene 
• 325460-66-0 (6R)-1-aza-6-[(tert-butyldimethylsiloxy)methyl]-4-phenyl-2-oxobicyclo[4.3.0]nonane 
• 325460-74-0 (2R)-2-[2'-(phenyl)-3'-(carbomethoxy)-propyl]proline methyl ester 
• 325460-61-5 (6R)-1-aza-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]nonane 
• 325460-75-1 (6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]nonane 

Relevant articles and documents

Allosteric modulation of the dopamine receptor by conformationally constrained type VI β-turn peptidomimetics of Pro-Leu-Gly-NH2

A peptidomimetic of Pro-Leu-Pro-NH2, 7, possessing an indolizidinone type VI β-turn mimic was synthesized via improved high-yielding protocols for the preparation and Cbz protection of α-allylproline. Bicyclic peptidomimetic 7 and spirobicylic

Novel bicyclic lactams as XaaPro type VI β turn mimics: Design, synthesis, and evaluation

The design, enantioselective synthesis, and structural characterization of novel bicyclic lactams as peptide mimics of the type VI β turn is described. The mimics duplicate the conformation of the backbone and disposition of the side-chain atoms of the central two residues of the turn. The Gly L-Pro mimic, lactam 6, was prepared in good overall yield starting from (S)-2-(2'-propenyl)proline. 1H NMR spectroscopy defined the relative stereochemistry of the substituents and conformational characteristics of the six-membered ring of the lactam; X-ray crystallographic analysis confirmed the conformational and stereochemical assignment. Examination of the crystal structure of lactam 6 revealed that the central amide bond was twisted appreciably out of planarity. The twisting of the amide bond was attributed to angle strain resulting from the presence of the sp2-hybridized nitrogen atom at the junction of the two rings. Alkylation of the enolate of the N,N-dimethylformamidine derivative of lactam 6 with benzyl bromide afforded stereoselectively the formamidine 11, a mimic of an L-Phe L-Pro dipeptide in the type VI turn conformation. The efficient synthetic route to highly functionalized peptidomimetics such as 11 will prove highly useful in peptide structure-function studies.