54793-80-5

Basic information

• Product Name: methyl prolylphenylalaninate
• CAS NO: 54793-80-5
• Molecular Formula: C₁₅H₂₀N₂O₃
• Molecular Weight: 276.3309
• Mol File: 54793-80-5.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 475.1°C at 760 mmHg
• Flash Point: 241.1°C
• Density: 1.156g/cm³
• Vapor Pressure: 3.43E-09mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: methyl prolylphenylalaninate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl prolylphenylalaninate(54793-80-5)
• EPA Substance Registry System: methyl prolylphenylalaninate(54793-80-5)

Safety Data

• Hazardous Substances Data: 54793-80-5(Hazardous Substances Data)

Upstream product

• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 63-91-2 L-phenylalanine 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 105414-01-5 Cbz-L-Pro-OCO₂-i-Bu 
• 147-85-3 L-proline 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 57177-79-4 (S)-tert-butyl 2-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl)pyrrolidine-1-carboxylate 
• 23631-72-3 N-carbobenzoxy-L-prolyl-L-phenylalanine methyl ester 

Downstream Products

• 1000591-21-8 Boc-Gly-Gly-Pro-Phe-Pro-Gly-OH 
• 919790-15-1 Boc-Gly-Gly-Pro-Phe-Pro-Gly-Tyr-OMe 
• 919790-20-8 Boc-Gly-Gly-Pro-Phe-Pro-Gly-Tyr-O-pnp 
• 246854-73-9 (S,S)-N-(4-dimethoxymethyl-benzoyl)proline-phenylalanine carboxylic acid hydrazide 
• 591208-36-5 (S,S)-N-(3-dimethoxymethyl-benzoyl)proline-phenylalanine carboxylic acid hydrazide 
• 82537-92-6 [(S)-2-((S)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-1-hydroxymethyl-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 78452-06-9 [(S)-1-((S)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-carbamic acid benzyl ester 
• 81531-47-7 [(S)-2-((S)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-1-benzyloxymethyl-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 81531-44-4 (6aR,9R,10aR)-7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid [(S)-1-((S)-3-benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-amide; compound with (Z)-but-2-enedioic acid 
• 81531-46-6 N-(9,10-Dihydrolysergyl-O-benzyl-L-seryl)-L-phenylalanyl-L-prolin-lactam 
• 50868-53-6 (6aR,9S)-7-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid [(S)-1-((S)-3-benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-amide 
• 50868-53-6 (6aR,9S)-7-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid [(S)-1-((S)-3-benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-amide 
• 50868-53-6 N-(d-Lysergyl-L-valyl)-L-phenylalanyl-D-prolin-lactam 
• 3705-26-8 L-Phenylalanyl-D-prolin-lactam 

Relevant articles and documents

Total syntheses of (?)-emestrin H and (?)-asteroxepin

First total syntheses of (?)-emestrin H and (?)-asteroxepin are described. To find the appropriate protecting group on the amide nitrogen of the diketopiperazine core, we conducted model studies using a simple diketopiperazine derivative. As a result, allyloxymethyl (Allom) group was the most suitable protecting group, which tolerated Nicolaou's sulfenylation conditions, and was easily cleavable under the mild conditions using Pd(PPh3)4 and N,N-dimethylbarbituric acid leaving methylthioethers intact. The general utility of Allom group for protection of amides was studied using simple substrates. Finally, the effectiveness of Allom group was proved by the accomplishment of the first total synthesis of (?)-emestrin H. Allom group was robust enough during installation of two methylthioethers to the diketopiperazine core and easily removed at the final step. The first total synthesis of (?)-asteroxepin was also completed by acylation of (?)-emestrin H.

Evaluation of two cyclic di-peptides as inhibitors of CCL2 induced chemotaxis

Monocyte chemoattractant protein (CCL2) plays a major role in the recruitment of monocytes during inflammation. In this study we analysed properties of synthetic CCL2 inhibitors in inhibiting CCL2 mediated monocyte migration. Using trans-endothelial chemotaxis assays compounds C1 and C5 were found to significantly reduce CCL2 mediated migration. Flow based adhesion assays showed reduction in adhesion to VCAM-1 in the presence of 10 nM CCL2 and 50 μM C5 (p 0.05). Further studies with these compounds can aid in their development as anti-inflammatory therapies. The Royal Society of Chemistry 2013.

Solvent-free asymmetric aldol reaction organocatalyzed by (S)-proline-containing thiodipeptides under ball-milling conditions

An efficient, solvent-free ball-milling protocol for the asymmetric aldol reaction between cyclohexanone and cyclopentanone with various aromatic aldehydes using a novel series of (S)-proline-containing dipeptides and thiodipeptides 1a-f as organocatalysts is reported. In general, (S)-proline-containing thiodipeptides proved to be better organocatalysts relative to their analogous amides. In particular, thiodipeptide (S,S)-1d catalyzed the stereoselective formation of the expected aldol products with excellent diastereo- and enantioselectivity (up to 98:2 anti/syn dr and up to 96% ee). This observation may be ascribed to the increased N-H acidity of the thioamide segment that leads to stronger H-bonding interaction with the aldehyde carbonyl at the transition state and thus higher stereoinduction. Furthermore, thiodipeptide 1f proved to be an efficient organocatalyst for the aldol reaction of acetone with isatin and isatin derivatives (ee 56-86%).