(S)-3-([1,1'-Biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid

Base Information

• Chemical Name: (S)-3-([1,1'-Biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid
• CAS No.: 147923-08-8
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.407
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID20375924
• Nikkaji Number: J1.178.193D
• Wikidata: Q72448711
• Mol file: 147923-08-8.mol

Synonyms:147923-08-8;Boc-L-4,4'-Biphenylalanine;Boc-4-phenyl-Phe-OH;(S)-3-([1,1'-Biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid;Boc-3-(4-Biphenylyl)-L-alanine;Boc-4-phenyl-L-phenylalanine;Boc-Bip-OH;BOC-4-BIPHENYL-L-ALA;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-phenylphenyl)propanoic acid;Boc-Bip(4,4')-OH;N-Boc-4-phenyl-L-phenylalanine;(S)-3-(biphenyl-4-yl)-2-(tert-butoxycarbonylamino)propanoic acid;N-(tert-Butoxycarbonyl)-4-phenyl-L-phenylalanine;Boc-D-Bip-OH;BOC-L-4,4'-BIPHENYLPHENYLALANINE;N-tert-Boc-L-biphenylalanine;MFCD00191184;BOC-BPH-OH;(2S)-2-{[(Tert-Butoxy)Carbonyl]Amino}-3-(4-Phenylphenyl)Propanoic Acid;Boc-L-4,4-biphenylalanine;SCHEMBL1325182;Boc-4-phenyl-Phe-OH, 97%;DTXSID20375924;NBVVKAUSAGHTSU-KRWDZBQOSA-N;AKOS015912048;AC-9869;HY-78843;PS-12517;Boc--(4-biphenylyl)-Ala-OH;B4289;CS-0009337;Boc-Bip(4,4 inverted exclamation mark )-OH;N12087;EN300-3404695;Nalpha-tert-butoxycarbonyl-4-phenyl-phenylalanine;A884385;J-008425;(S)-2-t-Butoxycarbonylamino-3-biphenyl-4-yl-propionic acid;(2S)-3-biphenyl-4-yl-2-tert-butoxycarbonylamino-propionic acid;(S)-2-(t-Butoxycarbonylamino)-3-(biphenyl-4-yl)propionic acid;(S)-2-t-butoxycarbonylamino-3-(biphenyl-4-yl)-propionic acid;N-alpha-t-Butyloxycarbonyl-L-biphenylalanine (Boc-L-Bip-OH);(S)-2(-t-butoxycarbonylamino)-3-(biphenyl-4-yl)-propionic acid;(S)-2-(t-butoxycarbonylamino)-3-(biphenyl-4-yl)-propionic acid;(S)-3-([1,1\'-Biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid;[1,1'-Biphenyl]-4-propanoic acid, alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-, (alphaS)-;3-(4-Biphenylyl)-N-(tert-butoxycarbonyl)-L-alanine;(2S)-3-([1,1'-Biphenyl]-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (non-preferred name)

Chemical Property of (S)-3-([1,1'-Biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid

Chemical Property:

• Vapor Pressure: 2.33E-12mmHg at 25°C
• Melting Point: 103-107 °C(lit.)
• Refractive Index: 1.555
• Boiling Point: 528.2 °C at 760 mmHg
• PKA: 3.88±0.10(Predicted)
• Flash Point: 273.2 °C
• Density: 1.161 g/cm³
• Storage Temp.: Store at RT.
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 341.16270821
• Heavy Atom Count: 25
• Complexity: 443

Purity/Quality:

97% ^*data from raw suppliers

N-Boc-4-phenyl-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: N,Xi,Xn
• Statements: 50/53-41-38-20/22-63
• Safety Statements: 60-61-36-26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)C2=CC=CC=C2)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)C2=CC=CC=C2)C(=O)O
• Uses: N-Boc-4-phenyl-L-phenylalanine is a reactant used in the synthesis of novel phenylalanines derived diamides as factor XIa inhibitors used in the treatment.

Technology Process of (S)-3-([1,1'-Biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid

There total 18 articles about (S)-3-([1,1'-Biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine (62129-39-9,79561-82-3) + phenylboronic acid (98-80-6) → N-tert-butoxycarbonyl-p-phenyl-L-phenylalanine (119273-61-9,128779-47-5,147923-08-8)

Guidance literature:

With dipotassium hydrogenphosphate; formic acid; Pd(OAc)2(2-amino-4,6-dihydroxypyrimidine disodium salt)2; In water; at 37 ℃; for 4h;

DOI:10.1021/ja907150m

Reference yield: 95.0%

N-Boc-4-I-Phe-OH (103882-09-3,62129-44-6) + phenylboronic acid (98-80-6) → N-tert-butoxycarbonyl-p-phenyl-L-phenylalanine (119273-61-9,128779-47-5,147923-08-8)

Guidance literature:

With dipotassium hydrogenphosphate; formic acid; Pd(OAc)2(2-amino-4,6-dihydroxypyrimidine disodium salt)2; In water; at 37 ℃; for 4h;

DOI:10.1021/ja907150m

Reference yield: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-3-([1,1'-biphenyl]-4-yl)-2-aminopropanoic acid (155760-02-4,170080-13-4) → N-tert-butoxycarbonyl-p-phenyl-L-phenylalanine (119273-61-9,128779-47-5,147923-08-8)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2018.10.041

upstream raw materials:

methyl (S)-3-([1,1'-biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoate

N-Boc-4-I-Phe-OH

phenylboronic acid

4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine

Downstream raw materials:

[(S)-2-Biphenyl-4-yl-1-(3-morpholin-4-yl-propylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

[(S)-2-Biphenyl-4-yl-1-((S)-1-phenyl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

(S)--β-alanine benzyl ester

Refernces

Structure-based design of dipeptide derivatives for the human neutral endopeptidase

10.1016/j.bmc.2011.08.064

The research focuses on the structure-based design of dipeptide derivatives as inhibitors for human neutral endopeptidase (NEP), an enzyme that plays a key role in the metabolic inactivation of various bioactive peptides. The study utilized the X-ray crystal structure of human NEP complexed with phosphoramidon to gain insights into the active site specificity of NEP. Using in silico molecular modeling, new inhibitors were designed and synthesized through short chemical steps. The designed compounds, including derivatives of N-(carboxymethyl)-L-phenylalanyl-b-alanine, were found to be highly effective with sub-nanomolar IC50 values, indicating the success of the structure-based molecular designing program. Key chemicals involved in the research include phosphoramidon, which was used as a reference inhibitor, and various amino acid derivatives such as Boc-3-(4-biphenylyl)-L-alanine and b-alanine benzyl ester p-toluenesulfonate, which were used in the synthesis of the designed inhibitors. The study also employed benzyl bromoacetate and formic acid in the synthesis process, and utilized molecular docking software like AutoDock 4.2 for computational design and analysis.

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