81177-54-0

Basic information

• Product Name: D-2-AMINO-5-METHYLHEX-4-ENOIC ACID
• Synonyms: D-2-AMINO-5-METHYLHEX-4-ENOIC ACID;(R)-2-AMino-5-Methylhex-4-enoic acid
• CAS NO: 81177-54-0
• Molecular Formula: C7H13NO2
• Molecular Weight: 143.18
• Mol File: 81177-54-0.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: D-2-AMINO-5-METHYLHEX-4-ENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: D-2-AMINO-5-METHYLHEX-4-ENOIC ACID(81177-54-0)
• EPA Substance Registry System: D-2-AMINO-5-METHYLHEX-4-ENOIC ACID(81177-54-0)

Safety Data

• Hazardous Substances Data: 81177-54-0(Hazardous Substances Data)

Usage

General Description

D-2-amino-5-methylhex-4-enoic acid, also known as 2-amino-5-methyl-4-pentenoic acid, is a chemical compound with a molecular formula of C7H13NO2. It is an amino acid derivative that is found in certain natural products and is predominantly used as a precursor in the synthesis of other compounds. This chemical is known for its role in the biosynthesis of the antibiotic mupirocin and has been used in the production of various pharmaceuticals and agricultural chemicals. D-2-amino-5-methylhex-4-enoic acid has also been studied for its potential biological activities and is of interest in drug discovery and development.

Upstream product

• 81136-75-6 (R)-2-Amino-5-methyl-hex-4-enoic acid methyl ester 
• 307304-48-9 (2S,4'S,5'R)-2-amino-1-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-methyl-4-hexen-1-one 
• 81136-56-3 (2S,5R)-2-(3,4-Dimethoxy-benzyl)-3,6-dimethoxy-2-methyl-5-(3-methyl-but-2-enyl)-2,5-dihydro-pyrazine 

Relevant articles and documents

1,5-dimethyl-4-phenylimidazolidin-2-one-derived iminic glycinimides: Useful new reagents for practical asymmetric synthesis of α-amino acids

New 1,5-dimethyl-4-phenylimidazolidin-2-one-derived acyclic chiral iminic glycine reagents have been prepared and diastereoselectively alkylated with activated alkyl halides and electrophilic olefins in the presence of lithium chloride under (a) strong bases (LHMDS, KOBu(t)) and low temperature (-78 °C,) conditions; (b) solid-liquid phase-transfer catalysis reaction (LiOH, TBAB, -20 °C) conditions, and (c) in the presence of organic bases (DBU, BEMP, TMG, -20 °C). In the case of dielectrophiles C- and N-alkylation takes place to afford heterocyclic derivatives. Hydrolysis of alkylated products has been carried out (a) in two-step procedures with LiOOH or LiOH followed by acidic hydrolysis or Dowex purification, (b) in one single-step under refluxing water to give the corresponding α-amino acid, (c) in the presence of DBU in methanol to provide N-protected α-amino acids methyl esters, or (d) by a protection-hydrolysis procedure to afford N-Boc-protected α-amino acids. The chiral imidazolidinone has generally been recovered in good yield. This methodology has been shown to be useful for the synthesis of acyclic and heterocyclic (S)- and (R)-α-amino acids.