2791-84-6

Basic information

• Product Name: L-Glutamic acid dibenzyl ester 4-toluenesulfonate
• Synonyms: GLU(OBZL)-OBZL TOS;GLUTAMIC ACID(OBZL)-OBZL P-TOSYLATE;H-GLU(OBZL)-OBZL 4-TOSYLATE;H-GLU(OBZL)-OBZL P-TOSYLATE;H-GLU(OBZL)-OBZL TOS;H-GLU(OBZL)-OBZL TOSOH;L-GLUTAMIC ACID GAMMA-BENZYL ESTER ALPHA-BENZYL ESTER TOSYLATE;L-GLUTAMIC ACID ALPHA,GAMMA-DIBENZYL ESTER 4-TOLUENESULFONATE SALT
• CAS NO: 2791-84-6
• Molecular Formula: C₇H₈O₃S*C₁₉H₂₁NO₄
• Molecular Weight: 499.58
• EINECS: 220-522-4
• Product Categories: Amino Acids Derivatives;Amino Acid Derivatives;Amino Acids;Glutamic acid [Glu, E];Amino Acids and Derivatives
• Mol File: 2791-84-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 142 °C
• Boiling Point: 453.5 °C at 760 mmHg
• Flash Point: 165.6 °C
• Appearance: /Powder
• Vapor Pressure: 2.06E-08mmHg at 25°C
• Storage Temp.: Store at RT.
• Solubility: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• CAS DataBase Reference: L-Glutamic acid dibenzyl ester 4-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: L-Glutamic acid dibenzyl ester 4-toluenesulfonate(2791-84-6)
• EPA Substance Registry System: L-Glutamic acid dibenzyl ester 4-toluenesulfonate(2791-84-6)

Safety Data

• Hazardous Substances Data: 2791-84-6(Hazardous Substances Data)

Usage

Description

L-Glutamic acid dibenzyl ester 4-toluenesulfonate is a chemical compound composed of L-glutamic acid, dibenzyl ester, and 4-toluenesulfonate. It is widely recognized for its role in organic chemistry as a reagent for the protection of carboxylic acids. L-Glutamic acid dibenzyl ester 4-toluenesulfonate serves as a versatile blocking group in the synthesis of peptides, ensuring stability and preventing unwanted side reactions. Its utility extends to the synthesis of pharmaceuticals and other organic compounds, making it an indispensable tool for chemists in the development of novel compounds and materials.

Uses

Used in Organic Chemistry:
L-Glutamic acid dibenzyl ester 4-toluenesulfonate is used as a protecting group for carboxylic acids during the synthesis of peptides. It provides stability to the carboxylic acid moiety and prevents unwanted reactions, ensuring the successful formation of the desired peptide sequence.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, L-Glutamic acid dibenzyl ester 4-toluenesulfonate is employed as a protecting group for carboxylic acids in the synthesis of various organic compounds. Its use facilitates the production of complex molecules with specific functional groups, contributing to the development of new drugs and therapeutic agents.
Used in Material Science:
L-Glutamic acid dibenzyl ester 4-toluenesulfonate also finds application in material science, where it is utilized in the synthesis of novel materials with unique properties. Its role as a protecting group for carboxylic acids allows for the controlled formation of complex structures, enabling the development of advanced materials for various applications.

InChI:InChI=1/C19H21NO4.C7H8O3S/c20-17(19(22)24-14-16-9-5-2-6-10-16)11-12-18(21)23-13-15-7-3-1-4-8-15;1-6-2-4-7(5-3-6)11(8,9)10/h1-10,17H,11-14,20H2;2-5H,1H3,(H,8,9,10)/t17-;/m0./s1

Upstream product

• 56-86-0 L-glutamic acid 
• 100-51-6 benzyl alcohol 
• 6893-26-1 D-Glutamic acid 
• 104-15-4 toluene-4-sulfonic acid 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 156078-80-7 (S)-2-{4-[Bis-(2-chloro-ethyl)-amino]-phenoxycarbonylamino}-pentanedioic acid dibenzyl ester 
• 194980-10-4 (S)-2-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester 
• 194980-11-5 (S)-2-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester 
• 215099-82-4 (S)-2-(Bis-benzyloxy-phosphanylamino)-pentanedioic acid dibenzyl ester 
• 869002-33-5 dibenzyl N-tert-butoxycarbonylglycyl-(D,L)-5,5-dimethylprolyl-L-glutamate 
• 869002-32-4 dibenzyl N-benzyloxycarbonyl-glycyl-L-4-thia-5,5-dimethylprolyl-L-glutamate 
• 869001-94-5 dibenzyl N-benzyloxycarbonyl-glycyl-L-2-methylprolyl-L-glutamate 
• 869001-96-7 dibenzyl N-benzyloxycarbonyl-glycyl-L-2-ethylprolyl-L-glutamate 
• 841233-65-6 dibenzyl N-(N-benzyloxycarbonyl-glycyl)-L-prolyl-L-glutamate 
• 869001-98-9 dibenzyl N-benzyloxycarbonyl-glycyl-L-2-allylprolyl-L-glutamate 
• 915193-97-4 (2S)-pent-4-enoylaminopentanedioic acid dibenzyl ester 
• 1007872-66-3 2-(benzyloxy-{3-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-propoxy}-phosphorylamino)-pentanedioic acid dibenzyl ester 
• 1007872-68-5 2-{benzyloxy-[3-(13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxy)-propoxy]-phosphorylamino}-pentanedioic acid dibenzyl ester 
• 1007872-69-6 2-{[3-(3-benzyloxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yloxy)-propoxy]-benzyloxy-phosphorylamino}-pentanedioic acid dibenzyl ester 

Relevant articles and documents

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.

CONJUGATES OF WATER SOLUBLE POLYMER-AMINO ACID OLIGOPEPTIDE-DRUG, PREPARATION METHOD AND USE THEREOF

A conjugate of water soluble polymer-amino acid oligopeptide-drug of Formula (I) below and a pharmaceutical composition comprising the conjugate are provided. In the conjugate, P is a water soluble polymer; X is a linking group, wherein the linking group links P and A1; each of A1, A2 and A3 is independently same or different amino acid residue or amino acid analogue residue; each of D1 and D2 is independently same or different drug molecule residue; a is 0 or 1; b is an integer of 2-12; c is an integer of 0-7; d is 0 or 1. The conjugate could improve drug load capacity, water solubility, stability and activity of the drug.

Synthesis of NO-NSAID dendritic prodrugs via Passerini reaction:new approach to the design of dendrimer-drug conjugates

We report the synthesis of a novel class of dendritic prodrugs via Passerini reaction in one pot. Such dendrimers feature a simultaneous attachment of a conventional non-steroidal anti-inflammatory drug (NSAID) (such as ibuprofen and aspirin) and a nitric oxide (NO)-releasing moiety (such as an organic nitrate) onto their surface, and are therefore regarded as new drug delivery systems for NO-releasing NSAIDs (NO-NSAIDs).