203873-67-0

Upstream product

• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 53793-18-3 (S)-2-(2-nitrophenylsulfonamido)-3-phenylpropanoic acid 
• 74-88-4 methyl iodide 
• 63-91-2 L-phenylalanine 

Downstream Products

• 203873-70-5 (S)-methyl 2-(N-allyl-2-nitrophenylsulfonamido)-3-phenylpropanoate 
• 283611-40-5 N-methyl-N-(o-nitrobenzenesulfonyl)-L-phenylalanine methyl ester 
• 1219815-36-7 C₂₀H₂₄N₂O₆S 
• 1219815-37-8 (S)-methyl 2-(N-decyl-2-nitrophenylsulfonamido)-3-phenylpropanoate 
• 1219815-35-6 methyl N-((2-nitrophenyl)sulfonyl)-N-propyl-L-phenylalaninate 
• 1219815-34-5 C₁₉H₁₈N₂O₆S 
• 1342305-88-7 N-(2-nitrophenyl)sulfonyl-N-phenethyl-L-Phe-OMe 
• 196214-70-7 N-phenethyl-L-Phe-OMe 
• 1342305-90-1 N-[(S)-2-chloropropionyl]-N-phenethyl-L-Phe-OMe 
• 1342305-92-3 (3S,4S)-4-benzyl-4-methoxycarbonyl-3-methyl-1-phenethyl-2-azetidinone 
• 1342305-86-5 (3S,4S)-4-benzyl-4-carboxy-3-methyl-1-phenethyl-2-azetidinone 
• 1312680-18-4 (3S,6S)-6-benzyl-3-methyl-1-propylpiperazine-2,5-dione 

Relevant academic research and scientific papers

DBU Catalysed Enantioselective Degradative Rearrangement: a Way to Tetrasubstituted 2-Aryl-2-Amino Esters

Herein we report a catalytic, easily scalable protocol for the enantioselective synthesis of Tetrasubstituted α-aryl-α-amino acid derivatives, using a biphasic system composed by catalytic DBU in DME and aqueous solutions of Na2CO3. Under very mild reaction conditions, without using metal or chiral additives, this heterogeneous system promotes the degradative rearrangement of functionalized N-aryl sulphonyl α-amino esters into the corresponding tetrasubstituted 2-aryl-2-amino esters, with high enantiomeric ratios (up to 97.5:2.5) and good yields (up to 95%). (Figure presented.).

Rhodium-Catalyzed Enantioselective Synthesis of Oxazinones via an Asymmetric Ring Opening-Lactonization Cascade of Oxabicyclic Alkenes

The rhodium-catalyzed asymmetric ring opening reaction of oxabicyclic alkenes is shown to be an efficient method for synthesizing chiral heterocycles. We demonstrate that the pairwise combination of chiral catalyst with chiral amino-acid-derived pronucleophiles results in a stereodivergent synthesis of diastereomeric hydroxyesters. A favorable conformational preference induces the subsequent lactonization of one diastereomer leading to the highly enantioselective synthesis of oxazinones.

Comparative Study of the Synthesis and Structural and Physicochemical Properties of Diketopiperazines vs Aza-diketopiperazines

Aza-diketopiperazines (aza-DKPs) represent an underprivileged motif obtained by scaffold hopping of 2,5-diketopiperazines (2,5-DKPs). Herein, we compare the synthesis and the structural and physicochemical properties of aza-DKP 4 vs 2,5-DKP 7. Thus, X-ray and 1H NMR studies show that aza-DKP 4 is a rigid and nonflat scaffold like the 2,5-DKP 7. Moreover, the replacement of one Cα-stereogenic center by a nitrogen atom results in a significant improvement of both the water solubility and the microsomal stability.

Synthesis of N-methyl L-phenylalanine for total synthesis of pepticinnamin e

The target compounds 3, 10 and 11 were synthesized through different N-methylation strategies. The concise and efficient preparation of them in large scale was developed and 3, 10 and 11 were obtained in suitable form used for both nitrogen-end and oxygen-end extension in next coupling reaction in peptides synthesis, specifically in total synthesis of natural pepticinnamin E.

Optically active 1,3,4,4-tetrasubstituted β-lactams: Synthesis and evaluation as tumor cell growth inhibitors

The in vitro cytotoxicity assays of several enantiopure (3S,4S)- and (3R,4R)-1,3,4,4-tetrasubstituted β-lactams derived from amino acids have shown that the (3S,4S)-4-benzyl-1-p-methoxybenzyl-3-methyl-4-methoxycarbonyl derivative 2a, obtained from Phe, displays significant activity, which is comparable to that of the anticancer drug Doxorubicin against HT29 cell lines. Modifications at positions 1 and 4 of the β-lactam ring led to identify the Tyr(2,6-ClBz) analogu 26d with similar activity data to those of 2a. The synthesis and SAR of all these tetrasubstituted β-lactams are reported here.

Convenient synthesis of N-methylamino acids compatible with Fmoc solid-phase peptide synthesis

Nα-Methylamino acid containing peptides exhibit interesting therapeutic profiles and are increasingly recognized as potentially useful therapeutics. Unfortunately, their synthesis is hampered by the high price and unavaibility of many Nα/

Microwave-accelerated cross-metathesis reactions of N-allyl amino acid substrates

Microwave heating has been utilised for the cross-metathesis reaction of N-allyl amino acid substrates to generate olefin homodimers. Remarkable acceleration of the cross-metathesis reaction (minutes compared to hours) over conventional reflux heating was

Amino acid derived intramolecular 1,3-dipolar cycloadditions that form bridged medium ring systems with diastereoselective control

Intramolecular nitrone cycloadditions using amino acid precursors, generate aminohydroxyazepine and amino hydroxypiperidine templates. The cycloaddition reactions yield either a [4.3.0] fused system or in most cases a [4.2.1] bridged system. The [4.2.1] bridged system allows for the stereospecific preparation of 3-amino-5-hydroxyazepines while the [4.3.0] system allows for the preparation of 3-amino-5-hydroxymethyl piperidines.

N-monoalkylation of α-amino acid esters under solid-liquid PTC conditions

N-(2-Nitrophenylsulfonyl)- (o-NBS-AA-OMe, 4) and N-(4- Nitrophenylsulfonyl)-α-amino acid methyl esters (p-NBSAA-OMe, 5) were N- alkylated with a variety of alkyl halides 6 under solid-liquid phase-transfer catalysis (SL-PTC) conditions, affording the alkylated products o-NBS-N-R2- AA-OMe 7 and p-NBS-N-R2-AA-OMe 8 in excellent yields without any detectable racemization.

Site-specific N-alkylation of peptides on the solid phase

A convenient approach, featuring a Mitsunobu reaction, is described for the introduction of an alkyl group at a specific amide function of a peptide on the solid phase. This 'site-specific alkylation' procedure is illustrated with an N-ethyl scan of Leu-enkephalin.