3-(Benzyloxycarbonylamino)-N-[alpha-(methoxycarbonyl)phenethyl]succinamidic acid

Base Information

• Chemical Name: 3-(Benzyloxycarbonylamino)-N-[alpha-(methoxycarbonyl)phenethyl]succinamidic acid
• CAS No.: 33605-72-0
• Molecular Formula: C22H24 N2 O7
• Molecular Weight: 428.442
• DSSTox Substance ID: DTXSID30955236
• Nikkaji Number: J31.501J
• Mol file: 33605-72-0.mol

Synonyms:DTXSID30955236;3-{[(Benzyloxy)(hydroxy)methylidene]amino}-4-hydroxy-4-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)imino]butanoic acid

Chemical Property of 3-(Benzyloxycarbonylamino)-N-[alpha-(methoxycarbonyl)phenethyl]succinamidic acid

Chemical Property:

• Boiling Point: 686.7°Cat760mmHg
• Flash Point: 369.1°C
• PSA: 138.01000
• Density: 1.29g/cm³
• LogP: 2.70130
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 428.15835111
• Heavy Atom Count: 31
• Complexity: 613

Purity/Quality:

99% ^*data from raw suppliers

Z-ASP-PHE-OME 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O)NC(=O)OCC2=CC=CC=C2

Technology Process of 3-(Benzyloxycarbonylamino)-N-[alpha-(methoxycarbonyl)phenethyl]succinamidic acid

There total 22 articles about 3-(Benzyloxycarbonylamino)-N-[alpha-(methoxycarbonyl)phenethyl]succinamidic 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: 100.0%

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + N-Cbz-L-Asp (1152-61-0) → N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester (33605-72-0)

Guidance literature:

thermolysin-immobilized capsule membrane; In chloroform; at 45 ℃; for 24h;

DOI:10.1039/P29880000091

Reference yield: 99.1%

→ methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester (33605-72-0)

Guidance literature:

Reference yield: 95.5%

N-Cbz-L-Asp (1152-61-0) → methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester (33605-72-0)

Guidance literature:

In N-methyl-acetamide; water;

upstream raw materials:

DL-phenylalanine methyl ester

N-benzyloxycarbonylaspartic acid

N-Cbz-L-Asp

methyl (2S)-2-amino-3-phenylpropanoate

Downstream raw materials:

N-[N-[(phenylmethoxy)carbonyl]-L-α-aspartyl]-L-phenylalanine 4-(1,1-dimethylethyl) 1-methyl ester

(Nα-benzyloxycarbonyl-Nγ-(β-D-glucopyranosyl)-L-asparaginyl)-L-phenylalanine methyl ester

(Nα-benzyloxycarbonyl-Nγ-{4-(β-D-glucopyranosyl)-β-D-glucopyranosyl}-L-asparaginyl)-L-phenylalanine methyl ester

(Nα-benzyloxycarbonyl-Nγ-{4-(α-D-glucopyranosyl)-β-D-glucopyranosyl}-L-asparaginyl)-L-phenylalanine methyl ester

Refernces

• 1、 Oyama, Kiyotaka,Nishimura, Shigeaki,Nonaka, Yuji,Kihara, Kei-ichi,Hashimoto, Tsutomu. "Synthesis of an Aspartame Precursor by Immobilized Thermolysin in an Organic Solvent". . p. 5241 - 5242. Retrieved 1981.
• 2、 Birrane, Gabriel,Bhyravbhatla, Balaji,Navia, Manuel A.. "Synthesis of aspartame by thermolysin: An x-ray structural study". . p. 706 - 710. Retrieved 2014.
• 3、 Yang, Chin-Ping,Su, Chein-Shyong. "Effects of Solvents and Additives on the Reaction of N-Benzyloxycarbonyl-L-Aspartic Anhydride with L-Phenylalanine Methyl Ester ( Synthesis of Aspartame)". . p. 5186 - 5191. Retrieved 1986.
• 4、 Crich, David,Sasaki, Kaname,Rahaman, Md Yeajur,Bowers, Albert A.. "One-pot syntheses of dissymmetric diamides based on the chemistry of cyclic monothioanhydrides. Scope and limitations and application to the synthesis of glycodipeptides". supporting information; experimental part. p. 3886 - 3893. Retrieved 2009/10/20.
• 5、 Kawasaki, Takayoshi,Hoshino, Yu,Ishizu, Yukari,Mizushiro, Yu,Okahata, Yoshio. "Control of hydrolysis and condensation activities of thermolysin by ultrasound irradiation". . p. 1602 - 1603. Retrieved 2007/10/03.