(S)-4-Amino-5-(benzyloxy)-5-oxopentanoic acid

Base Information

• Chemical Name: (S)-4-Amino-5-(benzyloxy)-5-oxopentanoic acid
• CAS No.: 13030-09-6
• Molecular Formula: C12H15NO4
• Molecular Weight: 237.255
• Hs Code.: 2922509090
• European Community (EC) Number: 692-605-7
• Nikkaji Number: J396.128A
• Mol file: 13030-09-6.mol

Synonyms:H-Glu-OBzl;13030-09-6;1-Benzyl L-Glutamate;(S)-4-Amino-5-(benzyloxy)-5-oxopentanoic acid;L-Glutamic Acid 1-Benzyl Ester;l-glutamic acid alpha-benzyl ester;(4S)-4-amino-5-(benzyloxy)-5-oxopentanoic acid;(4S)-4-amino-5-oxo-5-phenylmethoxypentanoic acid;H-L-Glu-OBzl;l-Glutamic acid, monobenzyl ester;4-Amino-5-(benzyloxy)-5-oxopentanoic acid;glutamic acid benzylester;SCHEMBL124387;g-(O-benzyl)-l-glutamic acid;L-Glutamic acid |A-benzyl ester;L-glutamic acid-mono-benzyl ester;MFCD00037312;AKOS015902939;AKOS015924090;CS-W009487;DS-2288;HY-W008771;AM20020382;B2996;4-Amino-5-(benzyloxy)-5-oxopentanoic acid #;EN300-243773

Chemical Property of (S)-4-Amino-5-(benzyloxy)-5-oxopentanoic acid

Chemical Property:

• Vapor Pressure: 1.15E-07mmHg at 25°C
• Melting Point: 157 °C
• Refractive Index: 1.555
• Boiling Point: 416 °C at 760 mmHg
• PKA: 4.21±0.10(Predicted)
• Flash Point: 205.4 °C
• PSA: 89.62000
• Density: 1.245 g/cm³
• LogP: 1.62220
• Storage Temp.: -15°C
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 261

Purity/Quality:

min 98.0% ^*data from raw suppliers

H-glu-OBzl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C(CCC(=O)O)N
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)[C@H](CCC(=O)O)N

Technology Process of (S)-4-Amino-5-(benzyloxy)-5-oxopentanoic acid

There total 10 articles about (S)-4-Amino-5-(benzyloxy)-5-oxopentanoic 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: 95.31%

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + benzyl alcohol (100-51-6,185532-71-2) → L-glutamic acid γ-benzyl ester (1676-73-9,25014-27-1) + 1-benzyl L-glutamate (13030-09-6)

Guidance literature:

With copper dichloride; at 60 ℃; for 2h; Reagent/catalyst; Solvent; Temperature; Catalytic behavior; Mechanism;

DOI:10.1016/j.catcom.2014.01.014

Reference yield: 89.0%

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + (4-hydroxyphenyl)(methyl)(benzyl)sulfonium chloride → 1-benzyl L-glutamate (13030-09-6)

Guidance literature:

With potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; for 8h; Ambient temperature;

DOI:10.1246/bcsj.69.1099

Reference yield:

dibenzyl L-glutamate (2768-50-5) → 1-benzyl L-glutamate (13030-09-6)

Guidance literature:

With hydrogen iodide; acetic acid;

DOI:10.1021/ja01114a528

upstream raw materials:

dibenzyl L-glutamate

Cbz-(L)-Glu-OBn

Tr-L-Glu(OBzl)-OH

L-glutamic acid

Downstream raw materials:

N-(N-benzyloxycarbonyl-L-γ-glutamyl)-L-glutamic acid-1-benzyl ester

Boc-Glu-OBn

(S)-2-pyrrol-1-yl-pentanedioic acid 1-benzyl ester

(S)-5-(benzyloxy)-4-(9H-carbazol-9-yl)-5-oxopentanoic acid

Refernces

• 1、 Zhao, Ming,Bi, Lanrong,Wang, Wei,Wang, Chao,Baudy-Floc'h, Michele,Ju, Jingfang,Peng, Shiqi. "Synthesis and cytotoxic activities of β-carboline amino acid ester conjugates". . p. 6998 - 7010. Retrieved 2006.
• 2、 Nakata, Takashi,Nakatani, Masaru,Takahashi, Masatoshi,Okai, Jiro,Kawaoka, Yoshiaki,Kouge, Katsushige,Okai, Hideo. "Peptide Synthesis in Aqueous Solution. V. Properties and Reactivities of (p-Hydroxyphenyl)benzylmethylsulfonium Salts for Direct Benzyl Esterification of N-Acylpeptides". . p. 1099 - 1106. Retrieved 2007/10/03.