6298-07-3

Basic information

• Product Name: methyl N~2~,N~5~-dibenzoyl-4-oxoornithinate
• CAS NO: 6298-07-3
• Molecular Formula: C₂₀H₂₀N₂O₅
• Molecular Weight: 368.3832
• Mol File: 6298-07-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 684.2°C at 760 mmHg
• Flash Point: 367.6°C
• Density: 1.236g/cm³
• Vapor Pressure: 1.42E-18mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: methyl N~2~,N~5~-dibenzoyl-4-oxoornithinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N~2~,N~5~-dibenzoyl-4-oxoornithinate(6298-07-3)
• EPA Substance Registry System: methyl N~2~,N~5~-dibenzoyl-4-oxoornithinate(6298-07-3)

Safety Data

• Hazardous Substances Data: 6298-07-3(Hazardous Substances Data)

Upstream product

• 6298-09-5 methyl 2,4,5-tribenzamido-4-pentenoate 
• 66675-21-6 methyl (2S)-2,4,5-tribenzamido-4-pentenoate 
• 71-00-1 L-histidine 
• 1499-46-3 L-Histidine methyl ester 

Downstream Products

• 2002-22-4 2-mercapto-L-histidine 
• 2481-04-1 L_s-threo-N²,N⁵-dibenzoyl-4-hydroxy-ornithine lactone 
• 16859-56-6 (S)-2,5-bis-benzoylamino-4-oxo-valeric acid 

Relevant articles and documents

Synthesis of Four Stereoisomers of γ-Hydroxyarginine via the Corresponding Isomers of γ-Hydroxyornithine

Diastereomeric-γ-hydroxy-L- and D-ornithines were prepared by reduction of the corresponding γ-oxoornithines synthesized from L- and D-histidines with sodium borohydride.The isomeric composition of the product obtained from L-histidine was estimated to be

PROCESS FOR THE SYNTHESIS OF L-(+)-ERGOTHIONEINE

This invention relates to a novel process for the preparation of optically pure L-(+)-ergothioneine. The process for the chemical synthesis of L-ergothioneine comprises steps which consist of reacting L-histidine alkyl ester with an acid halide, chloroformate or pyrocarbonate in the presence of a base, hydrolysis of the alkyl-(S,Z)-2,4,5-triamidopent-4-enoate to obtain a (S)-alkyl 2,5-diamido-4-oxopentanoate, acid catalyzed hydrolysis of the (S)-alkyl 2,5-diamido-4-oxopentanoate followed by reaction with a metal thiocyanate to obtain the thiohistidine, protection of the sulfur of thiohistidine as the tert-butyl thioether, dialkylation of the primary amine to obtain a tertiary amine, quaternization of the tertiary amine, and removal of the protecting group to obtain the desired (S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trialkylammonio)propanoate (I). This process affords a better yield and is capable of practical application at large scale.