169604-92-6

Basic information

• Product Name: (S)-3-tert-Butoxycarbonylamino-2-(toluene-4-sulfonylamino)-propionic acid methyl ester
• Synonyms: (S)-3-tert-Butoxycarbonylamino-2-(toluene-4-sulfonylamino)-propionic acid methyl ester
• CAS NO: 169604-92-6
• Molecular Weight: 372.442
• Mol File: 169604-92-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-3-tert-Butoxycarbonylamino-2-(toluene-4-sulfonylamino)-propionic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-tert-Butoxycarbonylamino-2-(toluene-4-sulfonylamino)-propionic acid methyl ester(169604-92-6)
• EPA Substance Registry System: (S)-3-tert-Butoxycarbonylamino-2-(toluene-4-sulfonylamino)-propionic acid methyl ester(169604-92-6)

Safety Data

• Hazardous Substances Data: 169604-92-6(Hazardous Substances Data)

Upstream product

• 16947-86-7 N^α-Tosyl-N^β-(tert-butpxycarbonyl)-L-α,β-diamonopropionic acid 
• 74-88-4 methyl iodide 
• 58457-98-0 methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoate 
• 36212-66-5 N²-(toluene-4-sulfonyl)-L-asparagine 
• 21753-19-5 2-(S)-p-toluenesulfonylamino-β-alanine 
• 98-59-9 p-toluenesulfonyl chloride 
• 77087-60-6 methyl (S)-2-amino-3-tert-butoxycarbonylaminopropanoate 

Downstream Products

• 175402-20-7 (S)-3-{[2-(4-Carbamimidoyl-phenyl)-benzooxazole-6-carbonyl]-amino}-2-(toluene-4-sulfonylamino)-propionic acid methyl ester 
• 175402-19-4 (S)-3-{[2-(4-Carbamimidoyl-phenyl)-benzooxazole-5-carbonyl]-amino}-2-(toluene-4-sulfonylamino)-propionic acid methyl ester 
• 175402-15-0 (S)-3-{[2-(4-Cyano-phenyl)-benzooxazole-6-carbonyl]-amino}-2-(toluene-4-sulfonylamino)-propionic acid methyl ester 
• 175402-26-3 (S)-3-{[2-(4-Cyano-phenyl)-benzooxazole-5-carbonyl]-amino}-2-(toluene-4-sulfonylamino)-propionic acid methyl ester 
• 169604-95-9 (S)-3-[3-(4-Cyano-phenoxymethyl)-benzoylamino]-2-(toluene-4-sulfonylamino)-propionic acid methyl ester 
• 169604-94-8 (S)-3-(3-Chloromethyl-benzoylamino)-2-(toluene-4-sulfonylamino)-propionic acid methyl ester 
• 199853-65-1 (S)-3-(3-methylbenzyl)amino-2-(4-toluenesulfonyl)amino-1-propanol 
• 199853-71-9 ethyl (S)-N-methyl-N-{3-[N-(3-methylbenzyl)-N-trifluoroacetyl]amino-2-(4-toluenesulfonyl)amino-1-propyl}aminoacetate 
• 199853-67-3 {[[(S)-3-Hydroxy-2-(toluene-4-sulfonylamino)-propyl]-(3-methyl-benzyl)-carbamoyl]-methyl}-methyl-carbamic acid tert-butyl ester 
• 199853-69-5 (S)-3-[N-(3-methylbenzyl)-N-trifluoroacetyl]amino-2-(4-toluenesulfonyl)amino-1-propanol 
• 199853-70-8 (S)-3-[N-(3-methylbenzyl)-N-trifluoroacetylaminomethyl]-1-(4-toluenesulfonyl)aziridine 
• 199853-76-4 N-[(S)-3-Hydroxy-2-(toluene-4-sulfonylamino)-propyl]-2-methylamino-N-(3-methyl-benzyl)-acetamide 
• 199853-72-0 (S)-N-methyl-N-[3-(3-methylbenzyl)-amino-2-(4-toluenesulfonyl)amino-1-propyl]aminoacetic acid 
• 199853-73-1 4-Methyl-N-[(R)-4-methyl-1-(3-methyl-benzyl)-2-oxo-[1,4]diazepan-6-yl]-benzenesulfonamide 

Relevant articles and documents

Design, synthesis, and in vitro activities of benzamide-core glycoprotein IIb/IIIa antagonists: 2,3-Diaminopropionic acid derivatives as surrogates of aspartic acid

In an effort to discover novel nonpeptide glycoprotein IIb/IIIa (GPIIb/IIa, α(IIb)/β3) inhibitors, we investigated RGD mimetics featuring a 3-substituted benzoic acid as the core, benzamidine as the basic moiety, and a series of β- and α-substituted β-alanine derivatives as aspartic acid surrogates. It was found that the use of β-methyl β-alanine slightly improved the anti-aggregant potency in human platelet-rich plasma over the unsubstituted β-alanine compound, while β-substitution with a trifluoromethyl group resulted in considerable loss in activity. Significant enhancement (up to 100-fold) in potency was obtained when the β-alanine was replaced with N2-substituted L-2,3-diaminopropionic acid derivatives. Among the three types of α-substituents (carbamate, amide, and sulfonamide) investigated, no apparent preference was observed with respect to in vitro potency. However, alkyl groups were more favorable than arylalkyl groups (Cbz) in the carbamate analogues. We also investigated piperidine, piperazine, and N-formamidinopiperidine as replacements for the benzamidine moiety. The former two replacements led to a drop in potency while the latter replacement resulted in maintenance of activity as compared with the corresponding benzamidine analogue.

Design, synthesis and in vitro activities of a series benzimidazole/benzoxazole glycoprotein IIb/IIIa inhibitors

A potent centrally constrained series of benzimidazole and benzoxazole glycoprotein IIb/IIIa inhibitors has been discovered based on the solution conformation of a cyclic RGD-containing peptide, DMP 728. The high potency of this series of compounds in the inhibition of platelet aggregation requires a benzamidine as the basic moiety and an α-carbamate or sulfonamide substituted β-alanine as the acidic moiety.