2886-33-1

Basic information

• Product Name: L-Aspartic acid dibenzyl ester 4-toluenesulfonate
• Synonyms: L-ASPARTIC ACID BETA-BENZYL ESTER ALPHA-BENZYL ESTER TOSYLATE;L-ASPARTIC ACID DIBENZYL ESTER 4-TOLUENESULFONATE SALT;L-ASPARTIC ACID DIBENZYL ESTER P-TOLUENESULFONATE;L-ASPARTIC ACID DIBENZYL ESTER P-TOLUENESULFONATE SALT;L-ASPARTIC ACID DIBENZYL ESTER TOLUENE-4-SULFONATE;L-ASPARTIC ACID ALPHA,BETA-BENZYL ESTER 4-TOLUENESULFONATE SALT;L-ASPARTIC ACID ALPHA,BETA-BENZYL ESTER P-TOLUENESULFONATE SALT;L-ASPARTIC ACID ALPHA,BETA-BENZYL ESTER TOLUENESULFONATE SALT
• CAS NO: 2886-33-1
• Molecular Formula: C₇H₇O₃S*C₁₈H₂₀NO₄
• Molecular Weight: 485.55
• EINECS: 220-746-2
• Product Categories: Amino Acids Derivatives;Amino Acids;Aspartic acid [Asp, D];Amino Acids and Derivatives;Amino Acids and Derivatives;Amino Acid Derivatives;Aspartic Acid;Peptide Synthesis
• Mol File: 2886-33-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 157-160 °C(lit.)
• Boiling Point: 455.3 °C at 760 mmHg
• Flash Point: 180.5 °C
• Appearance: Pale brown/Powder
• Vapor Pressure: 1.78E-08mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: Chloroform, DMSO, Methanol
• CAS DataBase Reference: L-Aspartic acid dibenzyl ester 4-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: L-Aspartic acid dibenzyl ester 4-toluenesulfonate(2886-33-1)
• EPA Substance Registry System: L-Aspartic acid dibenzyl ester 4-toluenesulfonate(2886-33-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 2886-33-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

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.

InChI:InChI=1/C18H19NO4.C7H8O3S/c19-16(18(21)23-13-15-9-5-2-6-10-15)11-17(20)22-12-14-7-3-1-4-8-14;1-6-2-4-7(5-3-6)11(8,9)10/h1-10,16H,11-13,19H2;2-5H,1H3,(H,8,9,10)/t16-;/m0./s1

Upstream product

• 56-84-8 L-Aspartic acid 
• 104-15-4 toluene-4-sulfonic acid 
• 100-51-6 benzyl alcohol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 7362-93-8 (S)-3-amino-4-(benzyloxy)-4-oxobutanoic acid 
• 1182-15-6 N^α-lauryl-L-aspartic acid dibenzyl ester 
• 70853-19-9 Boc-Val-Asp(OBzl)-OBzl 
• 104870-31-7 dibenzyl (2S)-2-({(2S)-4-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoyl}amino)butanedioate 
• 99429-23-9 BOC-Glu(OBzl)-Asp(OBzl)-OBzl 
• 5241-60-1 di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate 
• 56612-93-2 dibenzyl N-(tert-butoxycarbonyl)glycyl-L-aspartate 
• 1016549-35-1 C₁₉H₁₈N₄O₅ 
• 145435-30-9 N-tert-butoxycarbonyl-L-phenylalanine-L-aspartate dibenzyllester 
• 22828-04-2 N-benzyloxycarbonyl-L-phenylalanine-L-aspartate dibenzylester 
• 1105050-26-7 N-benzyloxycarbonyl-D-tryptophan-L-aspartate dibenzylester 
• 1186099-20-6 Boc-Asp(Asp(OBzl)OBzl)-Asp(OBzl)OBzl 
• 84668-69-9 (S)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-succinic acid dibenzyl ester 
• 1308670-92-9 C₂HF₃O₂*C₂₁H₂₄N₂O₅ 

Relevant articles and documents

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p-Toluenesulfonyl Chloride Catalysed Facile Synthesis of O-benzyl-l-amino Acids and Their In Vitro Evaluation

Protection and subsequent deprotection of amino acid functional groups play a key role in regioselective peptide synthesis. For protection, carboxylic acid functional groups are often benzylated using p-toluenesulfonic acid catalysed Fischer-Speier esterification reaction. Such reaction involves in situ water formation, which requires subsequent separation by azeotropic distillation for forward shift of equilibrium. To eliminate the need of this corresponding step requiring additional set-up, current study investigated p-toluenesulfonyl chloride as a reasonable alternative catalyst for facile benzylation of selected mono- and di- carboxylic amino acids. Literature reports that p-toluenesulfonyl chloride not only has a better shelf life but also demonstrates better safety in case of accidental systemic absorption over p-toluenesulfonic acid. As the O-benzyl-l-amino acids are often retained without deprotection to constitute the pharmaceutical peptide systems, synthesized compounds were investigated for their biocompatibility using in vitro cytotoxicity assays.

Polymorphism of amino acid-based dendrons: From organogels to microcrystals

There is a delicate balance for a low-weight molecule to behave as a gelator or crystal. The synthesis of two novel amino acid-based naphthalene-dendrons, Nap-G1 and Nap-G2 is described. Both dendrons display polymorphic properties in organic solvents. Nap-G1 developed a fibrous network with β-sheet architecture in cyclohexane but exhibited a spherulitic network in mixed solvents (chloroform/petroleum ether 1:5, v/v). On the other hand, Nap-G2 acted as an efficient organogelator in chloroform but formed crystalline fibers in relatively high polarity solvents (such as acetone and methanol). Combinations of characterizations have been employed to study the polymorphism. In the balance: Two amino acid-based naphthalene-dendrons display different polymorphic properties in organic solvents. Nap-G1 developed a fibrous network with β-sheet architecture in cyclohexane but exhibited a spherulitic network in mixed solvents while Nap-G2 acts as an efficient organogelator in chloroform but formed crystalline fibers in relatively high polarity solvents (see picture).