203873-67-0

Basic information

• Product Name: L-Phenylalanine, N-[(2-nitrophenyl)sulfonyl]-, methyl ester
• CAS NO: 203873-67-0
• Molecular Formula: C16H16N2O6S
• Molecular Weight: 364.379
• Mol File: 203873-67-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: L-Phenylalanine, N-[(2-nitrophenyl)sulfonyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, N-[(2-nitrophenyl)sulfonyl]-, methyl ester(203873-67-0)
• EPA Substance Registry System: L-Phenylalanine, N-[(2-nitrophenyl)sulfonyl]-, methyl ester(203873-67-0)

Safety Data

• Hazardous Substances Data: 203873-67-0(Hazardous Substances Data)

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 
• 63-91-2 L-phenylalanine 
• 53793-18-3 (S)-2-(2-nitrophenylsulfonamido)-3-phenylpropanoic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 203873-70-5 (S)-methyl 2-(N-allyl-2-nitrophenylsulfonamido)-3-phenylpropanoate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 1312680-18-4 (3S,6S)-6-benzyl-3-methyl-1-propylpiperazine-2,5-dione 
• 2439-60-3 N-methyl-L-phenylalanine methyl ester 
• 42267-32-3 2-nitro-benzenethiosulfonic acid S-phenyl ester 
• 1342305-86-5 (3S,4S)-4-benzyl-4-carboxy-3-methyl-1-phenethyl-2-azetidinone 
• 1342305-92-3 (3S,4S)-4-benzyl-4-methoxycarbonyl-3-methyl-1-phenethyl-2-azetidinone 
• 1342305-90-1 N-[(S)-2-chloropropionyl]-N-phenethyl-L-Phe-OMe 
• 196214-70-7 N-phenethyl-L-Phe-OMe 
• 1342305-88-7 N-(2-nitrophenyl)sulfonyl-N-phenethyl-L-Phe-OMe 
• 1219815-34-5 C₁₉H₁₈N₂O₆S 
• 1219815-35-6 methyl N-((2-nitrophenyl)sulfonyl)-N-propyl-L-phenylalaninate 

Relevant articles and documents

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.).

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.

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.