(S)-2-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid

Base Information

• Chemical Name: (S)-2-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid
• CAS No.: 127862-89-9
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.353
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID90426679
• Wikidata: Q72502130
• Mol file: 127862-89-9.mol

Synonyms:127862-89-9;Z-Homophe-OH;(S)-2-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid;Z-L-homophenylalanine;Cbz-L-homophenyl-Ala;Cbz-L-homoPhenylalanine;(2S)-4-phenyl-2-(phenylmethoxycarbonylamino)butanoic acid;(S)-2-(Z-amino)-4-phenylbutyric acid;MFCD00038796;Cbz-L-Homophe;Z-L-HomoPhe-OH;SCHEMBL2487005;BDBM36225;DTXSID90426679;GUWSQYJXSRIJCI-INIZCTEOSA-N;(2S)-2-{[(benzyloxy)carbonyl]amino}-4-phenylbutanoic acid;AKOS016842959;AM83539;CS-W012045;Z-Homophe-OH, >=98.0% (TLC);(N-carbobenzyloxy)-(L)-homophenylalanine;DS-17118;EN300-6747919;J-005550;(S)-2-(benzyloxycarbonylamino)-4-phenylbutanoic acid;(S)-2-(((BenZyloxy)carbonyl)amino)-4-phenylbutanoic acid (CbZ-L-hPhe-OH);Benzenebutanoic acid, alpha-[[(phenylmethoxy)carbonyl]amino]-, (alphaS)-

Chemical Property of (S)-2-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid

Chemical Property:

• Vapor Pressure: 9.79E-05mmHg at 25°C
• Refractive Index: 1.564
• Boiling Point: 324.8 °C at 760 mmHg
• PKA: 3.93±0.10(Predicted)
• Flash Point: 150.2 °C
• PSA: 75.63000
• Density: 1.164 g/cm³
• LogP: 3.38970
• Storage Temp.: Store at RT.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 313.13140809
• Heavy Atom Count: 23
• Complexity: 373

Purity/Quality:

98% ^*data from raw suppliers

Cbz-L-homophenylalanine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC(C(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)CC[C@@H](C(=O)O)NC(=O)OCC2=CC=CC=C2

Technology Process of (S)-2-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid

There total 8 articles about (S)-2-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic 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:

methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-4-phenylbutanoate (142037-77-2) → Z-homophenylalanine (83793-44-6,127862-89-9,135911-27-2,138812-70-1)

Guidance literature:

With lithium hydroxide; In methanol; water; at 0 - 20 ℃; for 8h;

DOI:10.1016/j.bmc.2015.09.029

Reference yield:

D-homophenylalanine (943-73-7) + phenylacetyl chloride (42940-68-1) → Z-homophenylalanine (83793-44-6,127862-89-9,135911-27-2,138812-70-1)

Guidance literature:

With sodium hydroxide; In water; at 0 - 20 ℃; for 4h; Inert atmosphere;

Reference yield:

(2S)-2-benzyloxycarbonylamino-4-phenylbutyric acid ethyl ester (288068-80-4) → Z-homophenylalanine (83793-44-6,127862-89-9,135911-27-2,138812-70-1)

Guidance literature:

With sodium hydroxide; In methanol; for 2h; Yield given; Ambient temperature;

DOI:10.7164/antibiotics.49.890

upstream raw materials:

(2S)-2-benzyloxycarbonylamino-4-phenylbutyric acid ethyl ester

benzyl chloroformate

L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride

D-homophenylalanine

Downstream raw materials:

(S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-hydroxy-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester

{(S)-1-[2-(4-Hydroxy-phenyl)-ethylcarbamoyl]-3-phenyl-propyl}-carbamic acid benzyl ester

[(S)-3-Phenyl-1-(2-p-tolyl-ethylcarbamoyl)-propyl]-carbamic acid benzyl ester

[(S)-1-(3,3-Diethoxy-propylcarbamoyl)-3-phenyl-propyl]-carbamic acid benzyl ester

Refernces

• 1、 Draper, Richard W.,Hou, Donald. "Novel stereoselective syntheses of the fused benzazepine dopamine D1 antagonist (6as,13br)-11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-5h-benzo[d]naphth[2,1-b] azepin-12-ol (sch 39166): 2. l-homophenylalanine-based syntheses". . p. 186 - 193. Retrieved 2013/09/08.
• 2、 Miyazawa, Toshifumi,Iwanaga, Hitoshi,Ueji, Shinichi,Yamada,Takashi,Kuwata, Shigeru. "Porcine Pancreatic Lipase Catalyzed Enantioselective Hydrolysis of Esters of N-Protected Unusual Amino Acids". . p. 2219 - 2222. Retrieved 2007/10/02.