432515-23-6

Basic information

• Product Name: t-butyl (S)-3-(4-hydroxy-3-nitrophenyl)-2-(3-trifluoromethyl-1-benzenesulfonylamino)-propionate
• Synonyms: t-butyl (S)-3-(4-hydroxy-3-nitrophenyl)-2-(3-trifluoromethyl-1-benzenesulfonylamino)-propionate
• CAS NO: 432515-23-6
• Molecular Weight: 490.457
• Mol File: 432515-23-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: t-butyl (S)-3-(4-hydroxy-3-nitrophenyl)-2-(3-trifluoromethyl-1-benzenesulfonylamino)-propionate(CAS DataBase Reference)
• NIST Chemistry Reference: t-butyl (S)-3-(4-hydroxy-3-nitrophenyl)-2-(3-trifluoromethyl-1-benzenesulfonylamino)-propionate(432515-23-6)
• EPA Substance Registry System: t-butyl (S)-3-(4-hydroxy-3-nitrophenyl)-2-(3-trifluoromethyl-1-benzenesulfonylamino)-propionate(432515-23-6)

Safety Data

• Hazardous Substances Data: 432515-23-6(Hazardous Substances Data)

Upstream product

• 432515-20-3 (S)-t-butyl 3-(4-hydroxyphenyl)-2-(3-trifluoromethylbenzenesulfonylamino)propionate 
• 777-44-6 3-(Trifluoromethyl)benzenesulfonyl chloride 
• 16874-12-7 Tyr(tBu) 

Downstream Products

• 1197191-38-0 (S)-2-(3-(4-(3-t-butoxy-3-oxo-2-(3-(trifluoromethyl)phenylsulfonamido)propyl)-2-nitrophenoxy)propylamino)pyridine 1-oxide 
• 1197191-42-6 C₃₅H₄₈F₃N₅O₁₁S 
• 1197191-35-7 (S)-t-butyl 3-(4-(4-t-butoxycarbonylaminobutoxy)-3-nitrophenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propionate 
• 798567-32-5 (S)-t-butyl 3-(4-(3-t-butoxycarbonylaminopropoxy)-3-nitrophenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propionate 
• 1197191-44-8 (S)-t-butyl 3-(4-(4-(t-butoxycarbonyl(4-methylpyridin-2-yl)amino)butoxy)-3-nitrophenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propanoate 
• 1197191-43-7 (S)-t-butyl 3-(4-(3-(1,3-dioxoisoindolin-2-yl)propoxy)-3-nitrophenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propanoate 
• 1197191-45-9 (S)-t-butyl 3-(4-(4-(2-methyl-1,3-dioxolan-2-yl)butoxy)-3-nitrophenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propanoate 
• 1197191-41-5 (S)-2-(4-(4-(3-t-butoxy-3-oxo-2-(3-(trifluoromethyl)phenylsulfonamido)propyl)-2-nitrophenoxy)butylamino)pyridine-1-oxide 
• 1197191-40-4 (S)-t-butyl 3-(4-(4-(t-butoxycarbonyl(4-methylpyridin-2-yl)amino)butoxy)-3-nitrophenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propanoate 
• 1197191-39-1 (S)-2-(4-(4-(3-t-butoxy-3-oxo-2-(3-(trifluoromethyl)phenylsulfonamido)propyl)-2-nitrophenoxy)butylamino)pyridine-1-oxide 
• 1197191-37-9 (S)-t-butyl 3-(3-nitro-4-(4-(pyrimidin-2-ylamino)butoxy)phenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propionate 
• 798567-51-8 t-butyl O-[2-(2-(2-(N-t-butoxycarbonyl)-2-aminoethoxy)ethoxy)ethyl]-meta-amino-N-[3-(trifluoromethyl)phenylsulfonyl]-L-tyrosinate 
• 798567-33-6 (S)-t-butyl 3-(4-(3-t-butoxycarbonylaminopropoxy)-3-aminophenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propionate 
• 216502-86-2 (S)-3-(4-Methoxy-3-nitro-phenyl)-2-(3-trifluoromethyl-benzenesulfonylamino)-propionic acid tert-butyl ester 

Relevant articles and documents

αvβ3 integrin-targeting Arg-Gly-Asp (RGD) peptidomimetics containing oligoethylene glycol (OEG) spacers

RGD peptides are used in biomaterials science for surface modifications with a view to elicit selective cellular responses. Our objective is to replace peptides by small peptidomimetics acting similarly. We designed novel molecules targeting αvβ3 integrin and featuring spacer-arms (for surface grafting), which do not disturb the biological activity, from (L) N-(3-(trifluoromethyl)benzenesulfonyl) tyrosine used as scaffold. Various Arg-mimics were fixed on the phenol function, and the ortho position was used for the coupling of OEG spacers. All peptidomimetics were active in the nM range in a binding test toward human αvβ 3 integrin (IC50 = 0.1 to 1.7 nM) and selective versus platelet integrin αIIbβ3. Selected compounds revealed excellent ability to inhibit bone cells adhesion on vitronectin. Modeling and docking studies were performed for comparing the most active RGD peptidomimetic to cilengitide, i.e., cyclo-[RGDfN(Me)V]-. Lastly, the adhesion of endothelial cells on a cultivation support grafted with RGD peptidomimetics was significantly improved. 2009 American Chemical Society.

Chemoselective O-methylation of N-acylated/sulfonylated tyrosine derivatives

Methyl ethers (6a and 6b) of N-trifluoroacetyl- and N-(m-trifluoromethyl) phenylsulfonyl-6-nitro-tyrosine t-butyl ester were readily prepared by modified Mitsunobu reaction (DPPE, DIAD, MeOH). Williamson (MeI, K2CO3 or Li2CO3 or NaOH under phase transfer) and classical Mitsunobu conditions (PPh3, DEAD, MeOH) gave O,N-dimethylated derivatives (7a and 7b) as side or main products. O- versus N-selectivity in tyrosine methylation reactions depends on both pKa values and steric factors.