(s)-Dibenzyl 2-aminosuccinate 4-methylbenzenesulfonate

Base Information

• Chemical Name: (s)-Dibenzyl 2-aminosuccinate 4-methylbenzenesulfonate
• CAS No.: 2886-33-1
• Molecular Formula: C18H19NO4^.C7H8O3S
• Molecular Weight: 485.558
• Hs Code.: 29224999
• European Community (EC) Number: 220-746-2
• Mol file: 2886-33-1.mol

Synonyms:2886-33-1;H-Asp(OBzl)-OBzl.TosOH;h-asp(obzl)-obzl tosoh;(s)-dibenzyl 2-aminosuccinate 4-methylbenzenesulfonate;l-aspartic acid dibenzyl ester tosylate;L-Aspartic acid dibenzyl ester p-toluenesulfonate salt;H-Asp(OBzl)-OBzl.Tos-OH;dibenzyl (2S)-2-aminobutanedioate;4-methylbenzenesulfonic acid;H-Asp(OBzl)-OBzl inverted exclamation mark currencyTosOH;L-Aspartic acid dibenzyl ester 4-toluenesulfonate;(s)-2-amino-succinic acid dibenzyl ester, p-tosylate;L-Aspartic Acid 1,4-Dibenzyl Ester p-Toluenesulfonate;MFCD00065188;NSC 602076;Asp(OBzl)-Obzl.TosOH;Maybridge1_003976;1,2-Bis(benzyloxycarbonyl)ethylammonium toluene-p-sulphonate;L-Aspartic acid dibenzyl ester p-toluenesulfonate;L-Aspartic acid, bis(phenylmethyl) ester, 4-methylbenzenesulfonate;SCHEMBL5396953;HMS552M16;C18H19NO4.C7H8O3S;aspartic acid dibenzyl ester tosylate;AKOS015895481;AKOS015924128;AM81638;CS-W014435;Dibenzyl L-aspartate p-toluenesulfonate;HY-W013719;dibenzyl L-aspartate paratoluenesulfonate;AC-19187;AS-12248;1,4-Dibenzyl L-Aspartate p-Toluenesulfonate;C18-H19-N-O4.C7-H8-O3-S;C2711;I10544;dibenzyl (S)-aspartate p-toluenesulfonic acid salt;l-aspartic acid dibenzyl ester p-tolue-nesulfonate;L-Aspartic acid, dibenzyl ester p-toluenesulfonate;dibenzyl (S)-aspartate p-toluene-sulfonic acid salt;J-300070;L-aspartic acid dibenzyl ester p-toluene sulfonic acid salt;L-Aspartic acid dibenzyl ester p-toluenesulfonate salt, 98%;1,4-dibenzyl (2S)-2-aminobutanedioate;4-methylbenzene-1-sulfonic acid

Chemical Property of (s)-Dibenzyl 2-aminosuccinate 4-methylbenzenesulfonate

Chemical Property:

• Vapor Pressure: 1.78E-08mmHg at 25°C
• Melting Point: 157-160 °C(lit.)
• Boiling Point: 455.3 °C at 760 mmHg
• Flash Point: 180.5 °C
• PSA: 141.37000
• LogP: 5.21340
• Storage Temp.: −20°C
• Solubility.: Chloroform, DMSO, Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 485.15082337
• Heavy Atom Count: 34
• Complexity: 580

Purity/Quality:

99% ^*data from raw suppliers

L-Aspartic acid dibenzyl ester p-toluenesulfonate salt ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.C1=CC=C(C=C1)COC(=O)CC(C(=O)OCC2=CC=CC=C2)N
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.C1=CC=C(C=C1)COC(=O)C[C@@H](C(=O)OCC2=CC=CC=C2)N
• Uses: L-Aspartic Acid Dibenzyl Ester p-Toluenesulfonate Salt is used in the preparation of Betulinic Acid derivatives that show inhibition towards HIV. It is also used in the preparation of piperidine funct ional amides which act as potent and highly selective human β3 agonists.

Technology Process of (s)-Dibenzyl 2-aminosuccinate 4-methylbenzenesulfonate

There total 4 articles about (s)-Dibenzyl 2-aminosuccinate 4-methylbenzenesulfonate 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%

L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6,185532-71-2) → dibenzyl L-aspartate toluene-4-sulphonate (2886-33-1)

Guidance literature:

In benzene; for 3.5h; Heating;

DOI:10.1021/jo00061a006

Reference yield: 87.0%

L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + p-toluenesulfonyl chloride (98-59-9) + benzyl alcohol (100-51-6,185532-71-2) → dibenzyl L-aspartate toluene-4-sulphonate (2886-33-1)

Guidance literature:

In cyclohexane; for 24h; Reflux;

DOI:10.1007/s10989-019-09998-x

Reference yield:

L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6,185532-71-2) → dibenzyl L-aspartate toluene-4-sulphonate (2886-33-1) + (R)-dibenzyl 2-aminosuccinate p-toluenesulfonic acid salt (4079-64-5)

Guidance literature:

In benzene; Solvent; Reflux;

DOI:10.1021/acs.oprd.5b00134

upstream raw materials:

L-Aspartic acid

toluene-4-sulfonic acid

benzyl alcohol

p-toluenesulfonyl chloride

Downstream raw materials:

N^α-t-Butoxycarbonyl-N^ε-benzyloxycarbonyl-L-lysyl-L-aspartic acid dibenzyl ester

Boc-Ser-Asp(OBzl)-OBzl

BocS(OBzl)D(OBzl)OBzl

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

Refernces

• 1、 Bolchi, Cristiano,Valoti, Ermanno,Fumagalli, Laura,Straniero, Valentina,Ruggeri, Paola,Pallavicini, Marco. "Enantiomerically Pure Dibenzyl Esters of l -Aspartic and l -Glutamic Acid". . p. 878 - 883. Retrieved 2015.
• 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.