118878-53-8

Basic information

• Product Name: D-ALL-ISOLEUCINE-METHYL ESTER HCL
• Synonyms: D-ALL-ISOLEUCINE-METHYL ESTER HCL;(2R,3S)-2-Amino-3-methyl-pentanoic acid methyl ester;(2R,3S)-methyl 2-amino-3-methylpentanoate(WXG02435)
• CAS NO: 118878-53-8
• Molecular Formula: C₇H₁₅NO₂
• Molecular Weight: 145.1995
• Mol File: 118878-53-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 169.2°C at 760 mmHg
• Flash Point: 42.7°C
• Appearance: /
• Density: 0.955g/cm³
• Vapor Pressure: 1.56mmHg at 25°C
• Refractive Index: 1.435
• PKA: 7.98±0.39(Predicted)
• CAS DataBase Reference: D-ALL-ISOLEUCINE-METHYL ESTER HCL(CAS DataBase Reference)
• NIST Chemistry Reference: D-ALL-ISOLEUCINE-METHYL ESTER HCL(118878-53-8)
• EPA Substance Registry System: D-ALL-ISOLEUCINE-METHYL ESTER HCL(118878-53-8)

Safety Data

• Hazardous Substances Data: 118878-53-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H15NO2/c1-4-5(2)6(8)7(9)10-3/h5-6H,4,8H2,1-3H3/t5-,6+/m0/s1

Upstream product

• 67-56-1 methanol 
• 1509-35-9 D-alloisoleucine 
• 60667-85-8 D-allo-isoleucine methyl ester hydrochloride 
• 1186663-68-2 N-nosyl-D-allo-isoleucine methyl ester 
• 1509-34-8 D-allo-isoleucine 
• 1356449-88-1 calyxamide B 
• 73-32-5 L-isoleucine 
• 56577-28-7 methyl (2S,3S)-2-hydroxy-3-methylpentanoate 
• 73-32-5 DL-isoleucine 
• 319-78-8 D-Isoleucine 

Downstream Products

• 872599-76-3 methyl N-[(2R)-2-(2,3-dihydro-1H-inden-2-yl)-2-({[(phenylmethyl)oxy]-carbonyl}amino)acetyl]-N-[1-(2,6-dimethyl-3-pyridinyl)-2-oxo-2-({2-[(phenylmethyl)oxy]phenyl}amino)ethyl]-D-alloisoleucinate 
• 1299957-27-9 methyl N-[(2,6-dimethyl-3-pyridinyl)methylidene]-D-alloisoleucine 
• 1412914-82-9 (2S,3aS,6R,7aS)-1-((2R,3S)-2-((R)-3-(4-(benzyloxy)phenyl)-2-((triisopropylsilyl)oxy)propanamido)-3-methylpentanoyl)-N-(4-(2,3-dibenzyloxycarbonyl)guanidinobutyl)-6-hydroxyoctahydro-1H-indole-2-carboxamide 
• 1412914-81-8 (2S,3aS,6R,7aS)-methyl-1-((2R,3S)-2-((R)-3-(4-(benzyloxy)phenyl)-2-((triisopropylsilyl)oxy)propanamido)-3-methylpentanoyl)-6-hydroxyoctahydro-1H-indole-2-carboxylate 
• 1412914-80-7 (2R,3S)-methyl 2-{(R)-3-[4-(benzyloxy)phenyl]-2-[(triisopropylsilyl)oxy]propanamido}-3-methylpentanoate 

Relevant articles and documents

N-Pyrazinoyl substituted amino acids as potential antimycobacterial agents-the synthesis and biological evaluation of enantiomers

Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with methyl or ethyl esters of selected amino acids. The antimicrobial activity was evaluated on a variety of (myco)bacterial strains, including Mtb H37Ra, M. smegmatis, M. aurum, Staphylococcus aureus, Pseudomonas aeruginosa, and fungal strains, including Candida albicans and Aspergillus flavus. Emphasis was placed on the comparison of enantiomer activities. None of the synthesized compounds showed any significant activity against fungal strains, and their antibacterial activities were also low, the best minimum inhibitory concentration (MIC) value was 31.25 μM. However, several compounds presented high activity against Mtb. Overall, higher activity was seen in derivatives containing l-amino acids. Similarly, the activity seems tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC 1.95 μg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds.

Total synthesis of aeruginosin 98B

The first total synthesis of aeruginosin 98B was accomplished. The key step is a highly diastereoselective Pd-catalyzed intramolecular asymmetric allylic alkylation reaction of a diastereomeric mixture of allylic carbonates that is enabled by the use of racemic phosphine ligand L1.

Deprotectlon of N-Nosyl-α-amlno acids by using solid-supported mercaptoacetic acid

A simple and efficient synthesis of a solid-supported thiol has been developed. Mercaptoacetic acid was first protected by the dimethoxytrityl group and then anchored to Wang resin through an ester bond. Deprotection of the thiol function led to resin-supported mercaptoacetic acid, a useful supported thiol reagent that can be used in the polymer-assisted solution-phase removal of nosyl (Ns) groups from the amino function of a-amino acids in peptide synthesis.