124842-28-0

Basic information

• Product Name: (R)-Methyl 4-aMino-2-((tert-butoxycarbonyl)aMino)-4-oxobutanoate
• Synonyms: (R)-Methyl 4-aMino-2-((tert-butoxycarbonyl)aMino)-4-oxobutanoate;Methyl N2-(tert-butoxycarbonyl)-D-asparaginate;Methyl (2S)-2-((tert-butoxycarbonyl)amino)-3-carbamoylpropanoate
• CAS NO: 124842-28-0
• Molecular Formula: C₁₀H₁₈N₂O₅
• Molecular Weight: 246.26032
• Mol File: 124842-28-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 447.189°C at 760 mmHg
• Flash Point: 224.252°C
• Appearance: /
• Density: 1.169g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.472
• Storage Temp.: 2-8°C(protect from light)
• PKA: 10.91±0.46(Predicted)
• CAS DataBase Reference: (R)-Methyl 4-aMino-2-((tert-butoxycarbonyl)aMino)-4-oxobutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Methyl 4-aMino-2-((tert-butoxycarbonyl)aMino)-4-oxobutanoate(124842-28-0)
• EPA Substance Registry System: (R)-Methyl 4-aMino-2-((tert-butoxycarbonyl)aMino)-4-oxobutanoate(124842-28-0)

Safety Data

• Hazardous Substances Data: 124842-28-0(Hazardous Substances Data)

Usage

General Description

(R)-Methyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate is a chemical compound that belongs to the class of amino acids. It is a derivative of the amino acid aspartate and is commonly used in organic synthesis and peptide chemistry. (R)-Methyl 4-aMino-2-((tert-butoxycarbonyl)aMino)-4-oxobutanoate is often utilized in the production of peptides and proteins and is also used as a reagent in the preparation of peptide-based drugs. The tert-butoxycarbonyl (Boc) protecting group in the structure allows for selective deprotection and manipulation of the compound during synthesis, making it a valuable tool in chemical research and drug development.

InChI:InChI=1/C10H18N2O5/c1-10(2,3)17-9(15)12-6(5-7(11)13)8(14)16-4/h6H,5H2,1-4H3,(H2,11,13)(H,12,15)/t6-/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 7536-55-2 N-tert-butyloxycarbonylasparagine 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 67-56-1 methanol 

Downstream Products

• 30044-67-8 L-t-Boc-Asnol 
• 61040-20-8 (S)-methyl 3-amino-2-((tert-butoxycarbonyl)amino)propanoate 
• 147091-70-1 methyl (S)-2-((t-butoxycarbonyl)amino)-3-cyanopropanoate 
• 6384-09-4 methyl (S)-2,4-diamino-4-oxobutanoate 
• 135339-70-7 N^α,N^α-bis(tert-butoxycarbonyl)-(S)-β-aspartyl-(S)-phenylalanine dimethyl ester 
• 135339-69-4 N^α,N^α-bis(tert-butoxycarbonyl)-N-benzyl-(S)-asparagine methyl ester 
• 550378-68-2 2-tert-butoxycarbonylamino-3-[3-(4-nitro-phenyl)-ureido]-propionic acid methyl ester 

Relevant articles and documents

Rotihibins, novel plant growth regulators from Streptomyces graminofaciens

In the course of screening search for plant growth regulators, a culture filtrate of Streptomyces graminofaciens 3C02 was found to inhibit the growth of lettuce seedlings. The active substances, named rotihibin A (1) and B (2), were revealed to be lipo-peptidal compounds. Rotihibins inhibit growth of various plants at below 1 μg/ml, but do not show lethal activity even at higher doses.

Studies on the constituents of Helleborus purpurascens: use of derivatives from calix[6]arene, homooxacalix[3]arene and homoazacalix[3]arene as extractant agents for amino acids from the aqueous extract

The task of this work was to investigate the extraction capacity of various calixarenes for free and esterified amino acids from aqueous acid phases. Furthermore, this method was applied to aqueous extracts of Helleborus purpurascens. Generally, it is known that calixarenes can be used as extractants for ammonium compounds due to π-cation and lone pair cation interactions. As first, tert-Butyl-calix[6]arene and derivatives thereof were used. They had already proven their worth in previous investigations. In addition, tert-Butyl-hexahomooxa-calix[3]arene was used also, which can also enter into lone pair cation interactions. In addition to these well-known calixarenes, new calixarenes were produced and tested. Based on the tert-Butyl-hexahomooxa-calix[3]arene, a phosphor(III)bridged derivative was prepared, combining the three aromatic hydroxyl groups to a phosphite. As a seldom-described class of calixarenes, tert-Butyl-hexahomoaza-calix[3]arene derivatives were used. The nitrogen analogues of tert-Butyl-hexahomooxa-calix[3]arene could be produced as N-benzyl derivatives. The structure of the esterified carboxymethylated derivative of N,N′,N″-Tribenzyl-tert-Butyl-hexahomoaza-calix[3]arene could be verified by X-ray structure analysis. It crystallized as a partial cone. The extraction capacity of the described calixarenes was investigated for amino acids from aqueous acidic solutions into an organic phase. For the testing were chosen asparagine, aspartic acid, tyrosine, tryptophane, phenylalanine and pipecolinic acid and their methyl esters. The amino acids and their methyl esters were dissolved in water at different pH values. The calixarenes were dissolved in dichloromethane (DCM) or chloroform. After this preparation, the aqueous acidic amino acid solutions were mixed with the solutions and shaken intensively. In addition, blank values were determined by extracting the aqueous stock solutions of the amino acids and their methyl esters with pure solvents. To determine the extraction rate, the phases were separated and each analysed using GC-FID, partially GC–MS(EI). The evaluation is performed in two ways. On the one hand the depletion in the aqueous phase and on the other hand the content in the organic phase was determined.

Ceric ammonium nitrate (CAN) mediated esterification of N-Boc amino acids allows either retention or removal of the N-Boc group

Reaction of N-Boc amino acids with ceric ammonium nitrate in an alcohol as the solvent at room temperature resulted in the esterification of N-Boc amino acids with Boc group retention. When the reaction was conducted at reflux temperature, esterification was accompanied with simultaneous removal of the Boc group. Both reactions gave the desired products in good yields.