1676-90-0

Basic information

• Product Name: Boc-L-aspartic acid 4-tert-butyl ester
• Synonyms: 4-tert-Butyl N-(tert-Butoxycarbonyl)-L-aspartate;N-(tert-Butoxycarbonyl)-L-aspartic Acid 4-tert-Butyl Ester 4-tert-Butyl N-Boc-L-aspartate N-Boc-L-aspartic Acid 4-tert-Butyl Ester Boc-Asp(OtBu)-OH;(2S)-4-tert-butoxy-2-[(tert-butoxycarbonyl)aMino]-4-oxobutanoic acid;N-Boc-L-aspartic acid 4-tert-butyl ester, 98%;N-tert-Butyloxycarbonyl-L-aspartic Acid β-tert-Butyl Ester;Boc-L-aspartic acid ?-tert-butyl ester99%;BOC-L-ASP(OTBU)-OH;BOC-L-ASP(TBU)-OH
• CAS NO: 1676-90-0
• Molecular Formula: C₁₃H₂₃NO₆
• Molecular Weight: 289.32
• Product Categories: Aspartic acid [Asp, D];Boc-Amino Acids and Derivative;Boc-Amino acid series
• Mol File: 1676-90-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 64-67 °C
• Boiling Point: 432.6 °C at 760 mmHg
• Flash Point: 215.4 °C
• Appearance: White/Powder
• Density: 1.139 g/cm³
• Vapor Pressure: 1.07E-08mmHg at 25°C
• Refractive Index: 1.47
• Storage Temp.: 2-8°C
• Solubility: Soluble in methanol and dimethyl sulfoxide.
• PKA: 3.69±0.23(Predicted)
• BRN: 2336144
• CAS DataBase Reference: Boc-L-aspartic acid 4-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-L-aspartic acid 4-tert-butyl ester(1676-90-0)
• EPA Substance Registry System: Boc-L-aspartic acid 4-tert-butyl ester(1676-90-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1676-90-0(Hazardous Substances Data)

Usage

Description

Boc-L-aspartic acid 4-tert-butyl ester is a chemical compound derived from aspartic acid, an amino acid that plays a crucial role in various biological processes. The compound is characterized by the presence of a Boc (tert-butyloxycarbonyl) protecting group and a 4-tert-butyl ester functional group, which contribute to its unique properties and reactivity.

Uses

Used in Pharmaceutical Industry:
Boc-L-aspartic acid 4-tert-butyl ester is used as a building block for the synthesis of various pharmaceutical compounds, particularly those involving aspartic acid or its derivatives. Its presence in the molecule allows for the creation of novel drug candidates with potential therapeutic applications.
Used in Biochemistry Research:
In the field of biochemistry, Boc-L-aspartic acid 4-tert-butyl ester serves as a valuable research tool for studying the interactions and functions of aspartic acid in biological systems. Its unique structure enables researchers to investigate the role of aspartic acid in enzyme catalysis, protein folding, and other biochemical processes.
Used in the Preparation of Thrombin Inhibitors:
Boc-L-aspartic acid 4-tert-butyl ester is used as a key intermediate in the synthesis of highly selective thrombin inhibitors. Thrombin is an enzyme involved in the blood clotting process, and its inhibition can be beneficial in the treatment of conditions such as deep vein thrombosis and acute coronary syndrome.
Used in the Preparation of Thiopeptides:
The compound is also utilized in the preparation of thiopeptides, which are a class of naturally occurring peptides containing sulfur atoms. Thiopeptides possess potent antibiotic and anticancer properties, making them an important area of research in the development of new therapeutic agents.
Used in the Preparation of Thioacylating Agents:
Boc-L-aspartic acid 4-tert-butyl ester is employed in the synthesis of thioacylating agents, which are compounds that can transfer a thioacyl group to another molecule. These agents are valuable in organic chemistry and have applications in the modification of proteins, nucleic acids, and other biomolecules, as well as in the development of new drugs and pharmaceuticals.

InChI:InChI=1/C13H23NO6/c1-12(2,3)19-9(15)7-8(10(16)17)14-11(18)20-13(4,5)6/h8H,7H2,1-6H3,(H,14,18)(H,16,17)/t8-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 3057-74-7 L-Asp(t-Bu) 
• 1913-12-8 β-tert-butyl-N-(tert-butoxycarbonyl)-L-aspartic acid dicyclohexylammonium salt 
• 36702-55-3 (S)-2-Benzyloxycarbonylamino-succinic acid 4-tert-butyl ester 1-ethyl ester 
• 2131-29-5 (S)-1-benzyl-4-tert-butyl 2-aminosuccinate 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 5545-52-8 Z-D(tBu)-OH 
• 130052-01-6 α-2-cyanoethyl N(α)-tert-butoxycarbonyl-L-aspartate 
• 30750-74-4 Boc-aspartic acid anhydride 
• 130074-09-8 Boc-Asp(OtBu)-OCet 
• 566188-97-4 Boc-Asp(OtBu)-OBn 
• 16965-08-5 1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate 
• 2673-19-0 4-tert-butyl 1-methyl L-aspartate hydrochloride 
• 146692-91-3 Z-aspartic acid alpha-tert-butyl ester 

Downstream Products

• 131368-08-6 tert-butoxycarbonyl-(β-tert-butyl)-L-aspartyl-L-phenylalanine thioamide 
• 92398-56-6 N-(tert-butyloxycarbonyl)-β-tert-butyl-L-aspartyl-D-α-aminobutyric acid benzyl ester 
• 92398-55-5 N-(tert-butyloxycarbonyl)-β-tert-butyl-L-aspartyl-D-alanine benzyl ester 
• 72594-93-5 α-<(benzyloxycarbonyl)hydrazidyl> β-tert-butyl tert-butyloxycarbonyl-L-aspartate 
• 92367-19-6 L-N-tert-butoxycarbonyl-β-tert-butylaspartyl-4'-(1-azi-2,2,2-trifluoroethyl)phenylalanine methyl ester 
• 184951-78-8 (S)-N-(2-Amino-5-nitro-phenyl)-3-tert-butoxycarbonylamino-succinamic acid tert-butyl ester 
• 247217-37-4 Boc-L-Asp(OtBu)-homo-β-L-Phe-OMe 
• 153287-86-6 (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid tert-butyl ester 
• 1802736-56-6 (3S)-3-[(tert-butoxycarbonyl)amino]-4-iodobutanoic acid tert-butyl ester 

Relevant articles and documents

BETA-SUBSTITUTED BETA-AMINO ACIDS AND ANALOGS AS CHEMOTHERAPEUTIC AGENTS

β-Substituted β-amino acids, β-substituted β-amino acid derivatives, and β-substituted β-amino acid analogs and (bio)isosteres and their use as chemotherapeutic agents are disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres are selective LAT1/4F2hc substrates and exhibit rapid uptake and retention in tumors expressing the LAT1/4F2hc transporter. Methods of synthesizing the β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and methods of using the compounds for treating cancer are also disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs exhibit selective uptake in tumor cells expressing the LAT1/4F2hc transporter and accumulate in cancerous cells when administered to a subject in vivo. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres exhibit cytotoxicity toward several tumor types.

METHOD FOR THE SYNTHESIS OF PEPTIDES WITHOUT SOLVENT

The disclosure relates to a method for the synthesis of a compound of the formula (I) in which: n is an integer higher than or equal to 1; Rb and each Rn are independently a hydrogen atom, a C1-C6 arylalkyl group or a C1-C6 alkyl group substituted or not by an aryl group, —COOH, C1-C6, —COO-(alkyl), —CONH2, —SH, heteroaryl, —NH2, —NHC(NH)(NH2), C1-C6-s-(alkyl), —OH or phenol; Ra is a N-protective group; Rc is a ORd group in which Rd is a C1-C6 alkyl group or a NReRf group in which Re and Rf Re independently an N-protective group.