L-alpha-Aspartyl-D-phenylalanine methyl ester

Base Information

• Chemical Name: L-alpha-Aspartyl-D-phenylalanine methyl ester
• CAS No.: 22839-65-2
• Molecular Formula: C14H18 N2 O5
• Molecular Weight: 294.307
• UNII: 83860AQE03
• Nikkaji Number: J525.427B
• ChEMBL ID: CHEMBL2110238
• Mol file: 22839-65-2.mol

Synonyms:L-alpha-Aspartyl-D-phenylalanine methyl ester;22839-65-2;83860AQE03;Methyl L-alpha-aspartyl-D-phenylalanate;alpha-L-Aspartyl-D-phenylalanine methyl ester;(3S)-3-amino-4-[[(2R)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid;L,D-Aspartame;SCHEMBL8761655;CHEMBL2110238;UNII-83860AQE03;D-Phenylalanine, N-L-alpha-aspartyl-, 1-methyl ester;.ALPHA.-L-ASPARTYL-D-PHENYLALANINE METHYL ESTER

Chemical Property of L-alpha-Aspartyl-D-phenylalanine methyl ester

Chemical Property:

• Vapor Pressure: 5.66E-15mmHg at 25°C
• Boiling Point: 594.4°Cat760mmHg
• Flash Point: 313.3°C
• PSA: 118.72000
• Density: 1.334g/cm³
• LogP: 0.78010
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 294.12157168
• Heavy Atom Count: 21
• Complexity: 380

Purity/Quality:

95% ^*data from raw suppliers

L-ALPHA-ASPARTYL-D-PHENYLALANINE METHYL ESTER 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)N
• Isomeric SMILES: COC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O)N

Technology Process of L-alpha-Aspartyl-D-phenylalanine methyl ester

There total 3 articles about L-alpha-Aspartyl-D-phenylalanine methyl ester 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:

N-phenacetyl-L-D-aspartame (104638-47-3) → phenylacetic acid (103-82-2) + α-L-aspartyl-D-phenylalanine methyl ester (22839-65-2,7421-84-3)

Guidance literature:

With pH 7.5; penicillinacylase on Eupergit C beads; In water; at 28 ℃; Yield given;

DOI:10.1016/S0040-4039(00)84751-6

Reference yield:

D-phenylalanine methyl ester (21685-51-8) → α-L-aspartyl-D-phenylalanine methyl ester (22839-65-2,7421-84-3)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylformamide

2: H₂, AcOH / Pd

With hydrogen; acetic acid; palladium; In N,N-dimethyl-formamide;

DOI:10.1021/ja01038a046

Reference yield:

N-Benzyloxycarbonyl-β-O-benzyl-Asp-D-Phe-methylester (22839-58-3) → α-L-aspartyl-D-phenylalanine methyl ester (22839-65-2,7421-84-3)

Guidance literature:

With hydrogen; acetic acid; palladium;

DOI:10.1021/ja01038a046

upstream raw materials:

N-Benzyloxycarbonyl-β-O-benzyl-Asp-D-Phe-methylester

N-phenacetyl-L-D-aspartame

D-phenylalanine methyl ester

Downstream raw materials:

neotame

3-Hydroxy-N-((S)-1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid

3-Hydroxy-N-((S)-1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid

Refernces