77457-02-4

Basic information

• Product Name: (S)-O-benzyl-α-methyltyrosine
• Synonyms: (S)-O-benzyl-α-methyltyrosine
• CAS NO: 77457-02-4
• Molecular Weight: 285.343
• Mol File: 77457-02-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-O-benzyl-α-methyltyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-O-benzyl-α-methyltyrosine(77457-02-4)
• EPA Substance Registry System: (S)-O-benzyl-α-methyltyrosine(77457-02-4)

Safety Data

• Hazardous Substances Data: 77457-02-4(Hazardous Substances Data)

Upstream product

• 302-72-7 rac-Ala-OH 
• 836-42-0 4-benzyloxybenzyl chloride 
• 672-87-7 L-methyltyrosine 
• 74825-83-5 Boc-(L)(α-Me)Tyr-OH 
• 100-39-0 benzyl bromide 
• 672-86-6 α-methyl-p-tyrosine 

Relevant articles and documents

(S)-ALPHA-FLUOROMETHYLTYROSINE AS DECARBOXYLASE INHIBITORS FOR USE IN THE TREATMENT OF HYPOTENSION

Provided are methods of using and drug delivery systems comprising inhibitors of pathogenic, bacterial metabolite production and conjugates of the inhibitors.

GENERAL METHOD FOR THE ASYMMETRIC SYNTHESIS OF α-AMINO ACIDS VIA ALKYLATION OF THE CHIRAL NICKEL(II) SCHIFF BASE COMPLEXES OF GLYCINE AND ALANINE

Nickel(II) complexes of Schiff bases derived from (S)-o-benzaldehyde and alanine (3), or (S)-O-benzophenone and alanine (4), or glycine (5) have been used for the asymmetric synthesis of α-amino acids under a variety of conditions.The method of choice consists of the reaction of the corresponding complex with the appropriate alkyl halide in DMF at 25 deg C using solid NaOH as a catalyst.Low diastereoselective excess (d.e.) is observed for the alkylation of complex (3) with benzyl bromide and allyl bromide.Large selectivity (80 percent) is observed for the alkylation of complex (4).Optically pure(R)- and (S)-O-benzyl-α-methyl-α-amino acids were obtained (70-90 percent) after the alkylated diastereoisomeric complexes had been seperated on SiO2 and hydrolysed with aqueous HCl.The initial chiral reagents were recovered (80-92 percent).The alkylation of complex (5) gave (S)-alanine, (S)-valine, (S)-phenylalanine, (S)-tryptophan, (S)-isoleucine, (S)-2-aminohexanoic acid, and 3,4-dimethoxyphenylalanine with optical yields of 70-92 percent.The optically pure α-amino acids were obtained after the separation of the alkylated diastereoisomeric complexes on SiO2.The stereochemical mechanism of the alkylation reaction is discussed.