Pentanoic acid, 4,5-diamino-5-oxo-, phenylmethyl ester, (R)-

Base Information

• Chemical Name: Pentanoic acid, 4,5-diamino-5-oxo-, phenylmethyl ester, (R)-
• CAS No.: 71811-14-8
• Molecular Formula: C₁₂H₁₆N₂O₃
• Molecular Weight: 236.271
• Mol file: 71811-14-8.mol

Synonyms:benzyl 4,5-diamino-5-oxopentanoate;D-γ-benzyl isoglutaminate;D-isoGln(OBn);D-isoglutamine benzyl ester;

Chemical Property of Pentanoic acid, 4,5-diamino-5-oxo-, phenylmethyl ester, (R)-

Chemical Property:

• Boiling Point: 446.3±45.0 °C(Predicted)
• PKA: 15.82±0.50(Predicted)
• PSA: 95.41000
• Density: 1.201±0.06 g/cm3(Predicted)
• LogP: 1.72320

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pentanoic acid, 4,5-diamino-5-oxo-, phenylmethyl ester, (R)-

There total 7 articles about Pentanoic acid, 4,5-diamino-5-oxo-, phenylmethyl ester, (R)- 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: 61.0%

Benzyl acetate (140-11-4) + D-α-glutamine (19522-40-8) → D-Glutaminsaeure-α-amid-γ-benzylester (71811-14-8,80064-48-8)

Guidance literature:

With perchloric acid; In water; for 12h; Inert atmosphere;

DOI:10.1016/j.bmcl.2010.08.056

Reference yield:

benzyl (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate (18800-73-2,19238-66-5) → D-Glutaminsaeure-α-amid-γ-benzylester (71811-14-8,80064-48-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.5h; Yield given; Ambient temperature;

Reference yield:

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid (35793-73-8) → D-Glutaminsaeure-α-amid-γ-benzylester (71811-14-8,80064-48-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 86.8 percent / dicyclohexylcarbodiimide (DCC) / ethyl acetate / 2 h / 0 °C

2: 70.8 percent / 25percent aq. ammonia / tetrahydrofuran / 2 h / Ambient temperature

3: CF₃COOH / 0.25 h / Ambient temperature

With ammonium hydroxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; ethyl acetate;

DOI:10.1246/bcsj.53.2570

upstream raw materials:

benzyl (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate

D-glutamic acid-5-benzyl ester

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid

N-tert-butoxycarbonyl-D-glutamic acid α-p-nitrophenyl-γ-benzyl ester

Downstream raw materials:

L-alanyl-(γ-benzyl ester D-isoglutamine)

muramyl dipeptide

(R)-4-(2-Amino-2-methyl-propionylamino)-4-carbamoyl-butyric acid benzyl ester

L-alanyl-D-isoglutamine