(S)-2-((2S,3S)-2-(((Benzyloxy)carbonyl)amino)-3-methylpentanamido)-3-phenylpropanoic acid

Base Information

• Chemical Name: (S)-2-((2S,3S)-2-(((Benzyloxy)carbonyl)amino)-3-methylpentanamido)-3-phenylpropanoic acid
• CAS No.: 13254-07-4
• Molecular Formula: C23H28N2O5
• Molecular Weight: 412.486
• European Community (EC) Number: 236-242-0
• DSSTox Substance ID: DTXSID10157615
• Nikkaji Number: J213.783F
• Wikidata: Q83025774
• Mol file: 13254-07-4.mol

Synonyms:13254-07-4;(S)-2-((2S,3S)-2-(((Benzyloxy)carbonyl)amino)-3-methylpentanamido)-3-phenylpropanoic acid;Z-Ile-Phe-OH;C23H28N2O5;EINECS 236-242-0;(2S)-2-[[(2S,3S)-3-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-3-phenylpropanoic acid;3-Phenyl-N-(N-((phenylmethoxy)carbonyl)-L-isoleucyl)-L-alanine;L-Phenylalanine,N-[(phenylmethoxy)carbonyl]-L-isoleucyl-;3-phenyl-N-[N-[(phenylmethoxy)carbonyl]-L-isoleucyl]-L-alanine;DTXSID10157615;AKOS015919716;(2S)-2-[(2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-methylpentanamido]-3-phenylpropanoic acid;CS-0444698;((Benzyloxy)carbonyl)-L-isoleucyl-L-phenylalanine;A888281;N-[N-[(Phenylmethoxy)carbonyl]-L-isoleucyl]-L-phenylalanine;(S)-2-((2S,3S)-2-(((Benzyloxy)carbonyl)amino)-3-methylpentanamido)-3-phenylpropanoicacid;(S)-2-((2S,3S)-2-(benzyloxycarbonylamino)-3-methylpentanamido)-3-phenylpropanoic acid

Chemical Property of (S)-2-((2S,3S)-2-(((Benzyloxy)carbonyl)amino)-3-methylpentanamido)-3-phenylpropanoic acid

Chemical Property:

• Vapor Pressure: 4.78E-18mmHg at 25°C
• Melting Point: 166-167 °C
• Refractive Index: 1.564
• Boiling Point: 654.9 °C at 760 mmHg
• PKA: 3.54±0.10(Predicted)
• Flash Point: 349.9 °C
• PSA: 104.73000
• Density: 1.193 g/cm³
• LogP: 3.92140
• Storage Temp.: -15°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 412.19982200
• Heavy Atom Count: 30
• Complexity: 556

Purity/Quality:

97% ^*data from raw suppliers

(S)-2-((2S,3S)-2-(((Benzyloxy)carbonyl)amino)-3-methylpentanamido)-3-phenylpropanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)NC(CC1=CC=CC=C1)C(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)NC(=O)OCC2=CC=CC=C2

Technology Process of (S)-2-((2S,3S)-2-(((Benzyloxy)carbonyl)amino)-3-methylpentanamido)-3-phenylpropanoic acid

There total 12 articles about (S)-2-((2S,3S)-2-(((Benzyloxy)carbonyl)amino)-3-methylpentanamido)-3-phenylpropanoic 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: 72.0%

H-Ile-Phe-OH (22951-98-0) + dimethylsulfonium methyl sulfate → N-Benzyloxycarbonyl-L-isoleucyl-L-phenylalanin (13254-07-4)

Guidance literature:

With sodium hydroxide; In water;

DOI:10.1246/bcsj.62.3103

Reference yield: 70.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + Z-Ile-OPfp (25529-36-6) → N-Benzyloxycarbonyl-L-isoleucyl-L-phenylalanin (13254-07-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; for 0.0111111h; microwave irradiation;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → N-Benzyloxycarbonyl-L-isoleucyl-L-phenylalanin (13254-07-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Et₃N / acetonitrile / 2 h / 5 °C

2: 72 percent / 1M NaOH / H₂O

With sodium hydroxide; triethylamine; In water; acetonitrile;

DOI:10.1246/bcsj.62.3103

upstream raw materials:

N-Cbz-L-Isoleucine

chloroformic acid ethyl ester

N-Benzyloxycarbonyl-L-isoleucyl-L-phenylalanin-2-iodethylester

H-Ile-Phe-OH

Downstream raw materials:

(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-phenyl-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

2'-N-(N-benzyloxycarbonyl-L-isoleucyl-L-phenylalanyl)-amino-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-adenosine

2'-N-(N-benzyloxycarbonyl-L-isoleucyl-L-phenylalanyl)-amino-2'-deoxyadenosine