CAS: 497-30-3; (S)-3-(2-Thioxo-2,3-Dihydro-1H-Imidazol-4-yl)-2-(Trimethylammonio)Propanoate

L-Histidine Methyl Ester Dihydrochloride置于palladium On Activated Charcoal 盐酸,Tea,氢气,碳酸氢钠,三乙胺,3-巯基丙酸,硫代氯甲酸苯酯体系中,用 四氢呋喃,二氯甲烷,水 作为反应溶剂,10.0~25.0 °C,506.62 Kpa 条件下,反应 80.5H,反应生成 麦角硫因
参考文献:Synthesis Of L-(+)-Ergothioneine
标题:Synthesis Of L-(+)-Ergothioneine
摘要:The First Synthesis Of L-(+)-Ergothioneine (1),A Rare Natural Amino Acid,Is Described. The Key Step Is The Direct Transformation Of The Imidazole Derivative 11 Into Imidazole-2-Thione 12. This Reaction Consists Of The Cleavage And The Re-Formation Of Imidazole Ring (Anrorc) With Phenyl Chlorothionoformate Via A Bamberger-Type Intermediate. The Conditions Used Are Mild Enough To Preserve The Asymmetric Center At The A-Carbon. The Release Of Enantiomerically Pure L-Ergothioneine (1) From The Ammonium Derivative 15 Was Performed Under Acidic Conditions To Avoid The Very Easy Racemization Of The Betaine Function. An Efficient And High-Yield Synthesis Of 2-Mercapto-L-Histidine (2) Which Uses The New Imidazole-2-Thione Formation Reaction Is Also Described.
DOI:10.1021/jo00125A014

专利信息

专利号:US-7767826-B2
优先权日:2007-10-05
标题 :Process for the synthesis of L-(+)-ergothioneine
发明人：TRAMPOTA MIROSLAV
权利人:PHARMATECH INTERNATIONAL INC
摘要: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.

专利号:US-2009093642-A1
优先权日:2007-10-05
标 题 :Process for the synthesis of l-(+)-ergothioneine

专利号:WO-2009045413-A1
优先权日:2007-10-05
标 题 :Process for the synthesis of l-(+)-ergothioneine