Synthesis and Properties of S-Aminomethylthiamine and N-Hydroxymethylthiamine

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概要

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• S-Aminomethylthiamine : N-[(2-Methyl-4-amino-5-pyrimidinyl) methyl]-N-[1-methyl-2-(dialkylaminomethyl) thio-4-hydroxy-1-butenyl] formamide (IIIa-d) were successfully synthesized by the reaction of an alkaline solution of thiamine (I) with chloroform solution of chloromethyldialkylamine (VIa-d), which were freshly prepared from methylenebisdialkylamine (Va-d) and acetyl chloride. The compounds (IIIa-d) were soluble in organic solvents and also soluble in water with the exception of IIIb. When III was dissolved in water, III afforded a small amount of cyclobismethylenethiamine (II) and mostly decomposed to I. The behaviour of IIIa in water was confirmed by means of polarographic technique. N-Hydroxymethylthiamine : 3-[(2-Methyl-4-hydroxymethylamino-5-pyrimidinyl)-methyl]-4-methyl-5-(2-hydroxyethyl) thiazolium chloride (VII) was also prepared from thiamine monochloride (I-Cl) and formalin. Compound VII gave also II in the presence of diethylamine. The formation pathway of II from I was also discussed.

• 公益社団法人日本薬学会の論文
• 1976-05-25

著者

• 安尾 悠紀

  Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.

• 安尾 悠紀

  Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.

関連論文

• A Convenient Synthesis of α-Substituted Cyclic α-Imino Acids
• Aminomethylation of Thiamine Disulfides and Formation of Cyclobismethylenethiamine from N-Aminomethylated Thiamine Disulfide
• The Reaction of S-Aminomethylthiamine with Acid Anhydride : The Synthesis of O, S-Bis (α-aminoacyl) thiamine
• Synthesis and Properties of S-Aminomethylthiamine and N-Hydroxymethylthiamine

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