N-Benzyloxycarbonyl-O-benzoyl Aspartame

Base Information

• Chemical Name: N-Benzyloxycarbonyl-O-benzoyl Aspartame
• CAS No.: 5262-07-7
• Molecular Formula: C29H30N2O7
• Molecular Weight: 518.566
• DSSTox Substance ID: DTXSID00447895
• Wikidata: Q82266795
• Mol file: 5262-07-7.mol

Synonyms:N-Benzyloxycarbonyl-O-benzoyl Aspartame;5262-07-7;benzyl (3S)-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxo-3-(phenylmethoxycarbonylamino)butanoate;DTXSID00447895;alpha-Benzyl-N-carbobenzoxy-L-aspartyl-L-phenylalanine Methyl Ester;3-(Carboxyamino)-N-(alpha-carboxyphenethyl)succinamic Acid Dibenzyl Methyl Ester

Chemical Property of N-Benzyloxycarbonyl-O-benzoyl Aspartame

Chemical Property:

• Melting Point: 118.5-119.5 °C
• Boiling Point: 727.7±60.0 °C(Predicted)
• PKA: 10.54±0.46(Predicted)
• PSA: 127.01000
• Density: 1.240±0.06 g/cm3(Predicted)
• LogP: 4.36010
• Solubility.: Chloroform, Dichloromethane, Methanol
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 15
• Exact Mass: 518.20530130
• Heavy Atom Count: 38
• Complexity: 756

Purity/Quality:

99% ^*data from raw suppliers

N-Benzyloxycarbonyl-O-benzoyl Aspartame ^*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)OCC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3
• Isomeric SMILES: COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)OCC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3
• Uses: Protected Aspartame derivative.

Technology Process of N-Benzyloxycarbonyl-O-benzoyl Aspartame

There total 10 articles about N-Benzyloxycarbonyl-O-benzoyl Aspartame 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: 92.5%

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + Z-Asp(OBzl)-OPyCl (122751-41-1) → Z-Asp(OBzl)-Phe-OMe (5262-07-7)

Guidance literature:

In 1,4-dioxane; Ambient temperature;

DOI:10.1248/cpb.37.46

Reference yield: 74.0%

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) + C26H25NO7PS2(1-) → Z-Asp(OBzl)-Phe-OMe (5262-07-7)

Guidance literature:

With TEA; In dichloromethane; at -60 ℃;

DOI:10.1016/S0040-4020(01)88631-2

Reference yield: 52.0%

Z-Asp(OBzl)-OH (3479-47-8) + methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) → Z-Asp(OBzl)-Phe-OMe (5262-07-7)

Guidance literature:

With dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III); [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; sodium hydrogencarbonate; triphenylphosphine; In dichloromethane; at 20 ℃; Inert atmosphere; Sealed tube; Irradiation;

DOI:10.1002/anie.202112668

upstream raw materials:

N-(benzyloxycarbonyl)-β-benzyl-L-aspartic acid p-nitrophenyl ester

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

Z-Asp(OBzl)-OH

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

Downstream raw materials:

Z-Aspt(OBzl)-Phe-OMe

C₃₈H₄₄N₄O₇

N,N-dimethyl-L-aspartyl-L-phenylalanine methyl ester

L-Asp-L-Phe-OMe

Refernces

• 1、 -. "Method for preparing amide from carboxylic acid under irradiation of blue light by taking iridium and cobalt complexes as catalysts". Paragraph 0113-0114. . Retrieved 2021/05/12.
• 2、 Tsuboi,Okada. "Amino acids and peptides. XXIII. Synthesis of N alpha-protected amino acid 6-chloro-2-pyridyl esters and their evaluation for peptide synthesis.". . p. 46 - 49. Retrieved 2007/10/02.