(S)-Dibenzyl 2-aminosuccinate

Base Information

• Chemical Name: (S)-Dibenzyl 2-aminosuccinate
• CAS No.: 2791-79-9
• Molecular Formula: C18H19NO4
• Molecular Weight: 313.353
• DSSTox Substance ID: DTXSID80384577
• Nikkaji Number: J301.794J
• Wikidata: Q72463585
• Mol file: 2791-79-9.mol

Synonyms:(S)-Dibenzyl 2-aminosuccinate;2791-79-9;Dibenzyl L-aspartate;L-ASPARTIC ACID DIBENZYL ESTER;dibenzyl (2S)-2-aminobutanedioate;H-ASP(OBZL)-OBZL HCL;Dibenzyl-l-aspartic acid;aspartic acid dibenzyl ester;6327-59-9;1,4-DIBENZYL (2S)-2-AMINOBUTANEDIOATE;dibenzyl aspartate;dibenzyl-l-aspartate;dibenzyl (S)-aspartate;Dibenzyl 2-aminosuccinate #;(S)-Dibenzyl2-aminosuccinate;SCHEMBL1264374;DTXSID80384577;AKOS024462516;CCG-256312;AS-57279;CS-0450394;A876841;BRD-K36568267-075-01-9

Chemical Property of (S)-Dibenzyl 2-aminosuccinate

Chemical Property:

• Boiling Point: 503.749 °C at 760 mmHg
• PKA: 5.77±0.33(Predicted)
• Flash Point: 258.458 °C
• PSA: 75.63000
• Density: 1.223 g/cm³
• LogP: 2.75380
• Solubility.: DCM
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 313.13140809
• Heavy Atom Count: 23
• Complexity: 373

Purity/Quality:

99%, ^*data from raw suppliers

DibenzylL-Aspartate ^*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)N
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)C[C@@H](C(=O)OCC2=CC=CC=C2)N
• Uses: Dibenzyl L-Aspartate is an protected intermediate of Aspartic Acid, an amino acid essential as the building blocks of proteins.

Technology Process of (S)-Dibenzyl 2-aminosuccinate

There total 13 articles about (S)-Dibenzyl 2-aminosuccinate 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: 83.2%

L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + benzyl alcohol (100-51-6,185532-71-2) → dibenzyl L-aspartate (2791-79-9)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 8h; Heating / reflux;

Reference yield:

dibenzyl N-(tert-butoxycarbonyl)glycyl-L-aspartate (56612-93-2) → BOC-glycine (4530-20-5) + dibenzyl L-aspartate (2791-79-9)

Guidance literature:

In various solvent(s); at 25 ℃; for 24h; Product distribution; Equilibrium constant; papain, ethylenediaminetetraacetic acid, L-cysteine, phosphate buffer; other solvents, other reaction temperatures and times;

Reference yield:

→ dibenzyl L-aspartate (2791-79-9) + (S)-benzyl 4-oxoazetidine-2-carboxylate (72776-05-7)

Guidance literature:

upstream raw materials:

di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate

L-Aspartic acid

benzyl alcohol

dibenzyl N-(tert-butoxycarbonyl)glycyl-L-aspartate

Downstream raw materials:

Boc-Val-Asp(OBzl)-OBzl

N-tert-butoxycarbonyl-L-leucyl-L-(α-O-benzylaspartate) benzyl ester

5-amino-1-(2',3'-O-isopropylidene-4'-hydroxymethylcyclopentyl)imidazole-4-dibenzyl aspartyl carboxamide

OC[Asp(OBzl)2]2

Refernces

• 1、 Choudhury, Pritam,Sarkar, Saheli,Das, Prasanta Kumar. "Tunable Aggregation-Induced Multicolor Emission of Organic Nanoparticles by Varying the Substituent in Naphthalene Diimide". . p. 14328 - 14341. Retrieved 2018/11/23.
• 2、 Soicke, Arne,Reuter, Cédric,Winter, Matthias,Neud?rfl, J?rg-Martin,Schl?rer, Nils,Kühne, Ronald,Schmalz, Hans-Günther. "Stereoselective Synthesis of Tricyclic Diproline Analogues that Mimic a PPII Helix: Structural Consequences of Ring-Size Variation". supporting information. p. 6467 - 6480. Retrieved 2016/02/18.