178744-39-3

Upstream product

• 67-56-1 methanol 
• 188624-28-4 (S)-N-trifluoroacetyl-4-fluoro-3-nitrophenylalanine 
• 78342-42-4 (S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine 
• 15017-52-4 4-(bromomethyl)-1-fluoro-2-nitrobenzene 
• 221123-51-9 4-fluoro-3-nitrobenzyl iodide 
• 188624-24-0 (RS)-N-trifluoroacetyl-4-fluoro-3-nitrophenylalanine methyl ester 
• 20367-99-1 ethyl 2-(acetylamino)-2-(ethoxycarbonyl)-3-(4'-fluoro-3'-nitrophenyl)propanoate 
• 459-57-4 4-fluorobenzaldehyde 
• 42564-51-2 4-fluoro-3-nitrobenzaldehyde 
• 20274-69-5 (4-fluoro-3-nitrophenyl)methanol 

Downstream Products

• 178744-40-6 (S)-2-[(R)-2-tert-Butoxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester 
• 193073-45-9 methyl 2-((tert-butoxycarbonyl)amino)-3-(4-fluoro-3-nitrophenyl)propanoate 
• 623941-89-9 (S)-2-[(S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-3-(3,4-dihydroxy-phenyl)-propionylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester 
• 178744-41-7 (S)-2-[(R)-2-tert-Butoxycarbonylamino-2-(4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester 
• 178744-42-8 (S)-2-[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3,5-diisopropoxy-4-methoxy-phenyl)-acetylamino]-2-(4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester 
• 178744-34-8 C₄₅H₄₉F₂N₇O₁₆ 
• 193074-08-7 [2-({(R)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester 
• 193074-12-3 [2-({(S)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester 
• 249757-19-5 (R)-[(S)-2-{[(S)-2-Amino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-(4-methoxy-phenyl)-acetic acid methyl ester 
• 193074-05-4 [2-{(R)-[amino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester 
• 249757-14-0 [2-({(R)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(S)-(4-methoxyphenyl)acetic acid methyl ester 
• 249757-20-8 (S)-[(S)-2-{[(R)-2-Amino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-(4-methoxy-phenyl)-acetic acid methyl ester 

Relevant academic research and scientific papers

Asymmetric Total Synthesis and Evaluation of Antitumor Activity of Ophiorrhisine A and Its Derivatives

The first asymmetric total synthesis of ophiorrhisine A (1), a new cyclic tetrapeptide isolated from Ophiorrhiza nutans, was accomplished via an intramolecular aromatic nucleophilic substitution reaction (IMSNAr) of a linear tripeptide to construct a 14-membered paracyclophane ring, resulting in confirmation of its structure and absolute configuration. The structure-activity relationship study of 1 and its derivatives demonstrated that some derivatives possessed cytotoxicity toward human cancer cell lines A549, HT29, and HCT116.

Synthetic studies towards the synthesis of western and eastern chloropeptin I, II subunits

The western subunit (16-membered ring) was synthesized by the intramolecular SNAr reaction while the first 16-membered ring compound was obtained as a model of the eastern subunit via an intramolecular Ni0 mediated coupling reaction.

Chemoenzymatic synthesis of enantiomerically pure 4-fluoro-3-nitro and 3-fluoro-4-nitro phenylallanine

Both antipodes of enantiomerically pure 4-fluoro-3-nitrophenylalanine and 3-fluoro-4-nitrophenylalanine were obtained from their corresponding racemates via enzymatic resolution.

Synthesis of a model of chloropeptins I, II western subunit by the intramolecular S(N)Ar based methodology

Formation of a biaryl ether bond between the termini of a tetrapeptide containing a highly racemization prone amino acid by the intramolecular SNAr reaction afforded two diastereomeric 16-membered macrocycles along with their respective atropoisomers. The (R,S,R) and its atropoisomer constituted model of chloropeptins I, II, western part.