103365-47-5

Usage

Uses

Used in Pharmaceutical Industry:
(S)-N-Boc-3-Amino-3-phenylpropanoic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in the Synthesis of Carnosine:
(S)-N-Boc-3-Amino-3-phenylpropanoic acid is used as a precursor in the synthesis of Carnosine (C184190), a naturally occurring dipeptide with antioxidant and anti-glycating properties. Carnosine has been studied for its potential role in preventing neurodegenerative diseases and other health benefits.
Used as a Sequestering Agent:
(S)-N-Boc-3-Amino-3-phenylpropanoic acid and its derivatives are used as selective and efficient sequestering agents for cytotoxic reactive carbonyl species. This application is particularly relevant in the development of therapeutic agents that can protect cells from oxidative stress and related damage.

InChI:InChI=1/C14H19NO4/c1-14(2,3)19-13(18)15-11(9-12(16)17)10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,15,18)(H,16,17)/p-1/t11-/m0/s1

Upstream product

• 614-19-7 (S)-3-amino-3-phenylpropanoic acid 
• 41840-28-2 S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine 
• 135865-77-9 (S)-N-(tert-Butoxycarbonyl)-1-phenyl-3-butenylamine 
• 124-38-9 carbon dioxide 
• 183990-25-2 ((R)-2-Chloro-1-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-52-7 benzaldehyde 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 150884-50-7 benzaldehyde N-boc imine 
• 591-51-5 phenyllithium 
• 126568-41-0 Benzyl-((1R,2S,3S)-4-benzyloxy-2,3-bis-methoxymethoxy-1-phenyl-butyl)-amine 
• 126568-43-2 Benzyl-((1R,2S,3S)-4-benzyloxy-2,3-dihydroxy-1-phenyl-butyl)-carbamic acid tert-butyl ester 
• 126610-77-3 (R)-tert-butyl N-<1-phenyl-2-<(p-toluenesulfonyl)oxy>ethyl>carbamate 
• 126568-42-1 (1R,2S,3S)-1-Benzylamino-4-benzyloxy-1-phenyl-butane-2,3-diol 

Downstream Products

• 532393-80-9 (3S)-N-Boc-3-amino-β-phenylalanine-L-valine-(4S)-methylsuccinimide 
• 945979-05-5 Boc-(S)-β³-hPhg-D-Oxd-OBn 
• 190189-97-0 methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropionate 

Relevant academic research and scientific papers

Configurationally Stable (S)- and (R)-α-Methylproline-Derived Ligands for the Direct Chemical Resolution of Free Unprotected β3-Amino Acids

Reported herein is a chemical method for the direct resolution of unprotected racemic β-substituted-β-amino acids (β3-AAs) that uses specially designed, stable, and recyclable α-methylproline-derived chiral ligands. The versatility of this methodology is unmatched by biocatalytic approaches. The method shows a broad synthetic generality for various aryl- or alkyl-substituted β3-AAs, and the new nonracemizable ligands can be accessed readily. Furthermore, the presented method produces an excellent stereochemical outcome and has a fully recyclable source of chirality, and the reaction conditions are operationally simple and convenient. The procedure has also been successfully applied to the scalable synthesis of the anti-HIV drug maraviroc.

Synthetic method for novel chiral ligand, metal chelate, multiple unnatural amino acids, maraviroc and key intermediate thereof

The invention discloses a synthetic method for a novel chiral ligand, a metal chelate, multiple unnatural amino acids, maraviroc and a key intermediate thereof. According to the synthetic method, (R)-2-methylproline is selected as a starting material, and asymmetrical resolution is induced by utilizing a nickel chelate, so that (S)-beta3-amino acid is obtained, and (S)-3-amino-3-phenylpropionic acid is taken as the key intermediate for synthesizing maraviroc, so that yield is high, and ee value reaches more than or equal to 98.2%. The method disclosed by the invention has the advantages that source of raw materials is wide, conditions of a synthetic process are mild, control is easy, and optical purity of products is high.

Ureidopeptide-based Bronsted bases: Design, synthesis and application to the catalytic enantioselective synthesis of β-amino nitriles from (arylsulfonyl)acetonitriles

The addition of cyanoalkyl moieties to imines is a very attractive method for the preparation of β-amino nitriles. We present a highly efficient organocatalytic methodology for the stereoselective synthesis of β-amino nitriles, in which the key to success is the use of ureidopeptide-based Bronsted base catalysts in combination with (arylsulfonyl)acetonitriles as synthetic equivalents of the acetonitrile anion. The method gives access to a variety of β-amino nitriles with good yields and excellent enantioselectivities, and broadens the stereoselective Mannich-type methodologies available for their synthesis. Learning from peptides: A concise route for the catalytic enantioselective synthesis of β-amino nitriles has been achieved by using ureidopeptide-based Bronsted bases as catalysts in the Mannich reaction of N-Boc imines and (arylsulfonyl)acetonitriles (see scheme; Boc=tert-butoxycarbonyl, napht=naphthyl, TMS=trimethylsilyl).

Chemical kinetic resolution of unprotected β-substituted β-amino acids using recyclable chiral ligands

The first chemical method for resolution of N,C-unprotected β-amino acids was developed through enantioselective formation and disassembly of nickel(II) complexes under operationally convenient conditions. The specially designed chiral ligands are inexpensive and can be quantitatively recycled along with isolation of the target β-substituted-β-amino acids in good yields and excellent enantioselectivity. The method features a broad synthetic generality including β-aryl, β-heteroaryl, and β-alkyl-derived β-amino acids. The procedure is easily scaled up, and was used for the synthetically and economically advanced preparation of the anti-diabetic drug sitagliptin. The nick of time: A chemical method for resolution of unprotected β-amino acids rac-1 was developed through enantioselective formation and disassembly of nickel(II) complexes to deliver the target β-substituted β-amino acids in good yields and excellent enantioselectivity. The chiral ligands are inexpensive and can be quantitatively recycled. The procedure was used for the preparation of anti-diabetic drug sitagliptin.

SONIC HEDGEHOG MODULATORS

Sonic Hedgehog modulators and methods of use thereof are provided for.

Asymmetric biocatalysis of S-3-amino-3-phenylpropionic acid with new isolated Methylobacterium Y1-6

β-amino acids are widely used in drug research, and S-3-amino-3-phenylpropionic acid (S-APA) is an important pharmaceutical intermediate of S-dapoxetine, which has been approved for the treatment of premature ejaculation. Chiral catalysis is an excellent method for the preparation of enantiopure compounds. In this study, we used (±)-ethyl-3-amino-3-phenylpropanoate (EAP) as the sole carbon source. Three hundred thirty one microorganisms were isolated from 30 soil samples, and 17 strains could produce S-APA. After three rounds of cultivation and identification, the strain Y1-6 exhibiting the highest enantioselective activity of S-APA was identified as Methylobacterium oryzae. The optimal medium composition contained methanol (2.5 g/L), 1,2-propanediol (7.5 g/L), soluble starch (2.5 g/L), and peptone (10 g/L); it was shaken at 220 rpm for 4-5 days at 30 C. The optimum condition for biotransformation of EAP involved cultivation at 37 C for 48 h with 120 mg of wet cells and 0.64 mg of EAP in 1 ml of transfer solution. Under this condition, substrate ee was 92.1% and yield was 48.6%. We then attempted to use Methylobacterium Y1-6 to catalyze the hydrolytic reaction with substrates containing 3-amino-3-phenyl-propanoate ester, N-substituted-β-ethyl-3-amino-3-phenyl-propanoate, and γ-lactam. It was found that 5 compounds with ester bonds could be stereoselectively hydrolyzed to S-acid, and 2 compounds with γ-lactam bonds could be stereoselectively hydrolyzed to (-)-γ-lactam.

Organocatalytic asymmetric mannich reactions with JV-Boc and JV-Cbz protected α-amido sulfones (Boc: Tert-butoxycarbonyl, Cbz: Benzyloxycarbonyl)

Different malonates and βketoesters can react with N-tert-butoxycarbonyl- (N-Boc) and N-benzyloxycarbonyl- (N-Cbz) protected α-amido sulfones in an organocatalytic asymmetric Mannich-type reaction. The reaction makes use of a simple and easily obtained ph

Iridium(I)-catalyzed regio- and enantioselective allylic amidation

Ir(I)-catalyzed intermolecular allylic amidation of ethyl allyl carbonates with soft nitrogen nucleophiles under completely 'salt-free' conditions is described. A combination of [Ir(COD)Cl]2, a chiral phosphoramidite ligand L*, and DBU as a base in THF effects the reaction. The reaction appears to be quite general, accommodating a wide variety of R-groups and soft nitrogen nucleophiles, and proceeds with excellent regio- and enantioselectivities to afford the branched N-protected allylic amines. The developed reaction was conveniently utilized in the asymmetric synthesis of N-Boc protected α- and β-amino acids as well as (-)-cytoxazone.

The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: Enantioselective synthesis of β-amino acids

We describe the first efficient, direct asymmetric Mannich reactions with malonates and N-Boc aryl and alkyl imines by cooperative hydrogen-bonding catalysis with a cinchona alkaloid bearing a thiourea functionality. We have also extended the scope of thi