Dibenzyl 2-(phenylmethoxycarbonylamino)butanedioate

Base Information

• Chemical Name: Dibenzyl 2-(phenylmethoxycarbonylamino)butanedioate
• CAS No.: 5241-60-1
• Molecular Formula: C26H25NO6
• Molecular Weight: 447.488
• Hs Code.: 2924299090
• NSC Number: 118539
• ChEMBL ID: CHEMBL1864216
• Mol file: 5241-60-1.mol

Synonyms:MLS002706797;dibenzyl 2-(phenylmethoxycarbonylamino)butanedioate;SMR001574196;NSC118539;cid_273367;SCHEMBL8765627;CHEMBL1864216;dibenzyl (2S)-2-(phenylmethoxycarbonylamino)butanedioate;BDBM91433;AKOS015895816;NSC-118539;FT-0654330;2-(benzyloxycarbonylamino)succinic acid dibenzyl ester;bis(phenylmethyl) 2-(phenylmethoxycarbonylamino)butanedioate;2-(phenylmethoxycarbonylamino)butanedioic acid bis(phenylmethyl) ester

Chemical Property of Dibenzyl 2-(phenylmethoxycarbonylamino)butanedioate

Chemical Property:

• Vapor Pressure: 6.7E-15mmHg at 25°C
• Refractive Index: 1.585
• Boiling Point: 611.7 °C at 760mmHg
• Flash Point: 323.7 °C
• PSA: 90.93000
• Density: 1.234 g/cm³
• LogP: 4.54920
• Storage Temp.: Store at 0-5°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 447.16818752
• Heavy Atom Count: 33
• Complexity: 606

Purity/Quality:

98%min ^*data from raw suppliers

(S)-Dibenzyl2-(((benzyloxy)carbonyl)amino)succinate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)CC(C(=O)OCC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3

Technology Process of Dibenzyl 2-(phenylmethoxycarbonylamino)butanedioate

There total 9 articles about Dibenzyl 2-(phenylmethoxycarbonylamino)butanedioate 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: 95.0%

dibenzyl L-aspartate toluene-4-sulphonate (2886-33-1) + benzyl chloroformate (501-53-1,94274-21-2) → di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate (5241-60-1)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; for 18h; Ambient temperature;

DOI:10.1021/jm9601009

Reference yield: 88.0%

N-Cbz-L-Asp (1152-61-0) + benzyl bromide (100-39-0) → di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate (5241-60-1)

Guidance literature:

With sodium hydroxide; 15-crown-5; In N,N-dimethyl-formamide; at 40 ℃; for 2h;

DOI:10.1007/BF00574742

Reference yield:

N-Cbz-L-Asp (1152-61-0) + benzyl alcohol (100-51-6,185532-71-2) → di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate (5241-60-1)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1021/ja00988a043

upstream raw materials:

N-benzyloxycarbonylaspartic acid

N-Cbz-L-Asp

benzyl bromide

dibenzyl L-aspartate toluene-4-sulphonate

Downstream raw materials:

β-benzyl N-benzyloxycarbonyl-DL-aspartate

N-(O-benzyl-N-benzyloxycarbonyl-L-α-aspartyl)-L-leucine benzyl ester

N-(O-benzyl-N-benzyloxycarbonyl-L-α-aspartyl)-L-aspartic acid dibenzyl ester

N-(O-benzyl-N-benzyloxycarbonyl-L-α-aspartyl)-L-glutamic acid dibenzyl ester

Refernces

• 1、 Parr, Ian B.,Boehlein, Susan K.,Dribben, Anthony B.,Schuster, Sheldon M.,Richards, Nigel G. J.. "Mapping the aspartic acid binding site of Escherichia coli asparagine synthetase B using substrate analogs". . p. 2367 - 2378. Retrieved 2007/10/03.
• 2、 Mazurov, A. A.,Antonenko, S. V.,Andronati, S. A.. "PREPARATION OF ESTERS OF AMINO ACIDS AND OF PEPTIDES UNDER MILD CONDITION". . p. 208 - 210. Retrieved 2007/10/02.