Vitamin B₁及び諸關係化合物の研究 (第43報)

Allithiamine同族体の合成 その2

抄録

Eleven kinds of 2-[2′-methyl-4′-aminopyrimidyl-(5′)]-methyl-formamino-5-hydroxy-Δ²-pentenyl-(3) alkyl disulfide (thiamine alkyl disulfide) (I) were prepared by the reaction of the aqueous solution of the sodium salt (III) of thiol form of thiamine and sodium alkyl thiosulfate (II) (Bunte's salt). When the alkyl was methyl, ethyl, propyl, or allyl, the reaction mixture was saturated with sodium chloride. This reaction occurred with ease at room temperature and the yields were generally 80-95%. Use of homothiamine instead of thiamine yielded five kinds of 2-[2′-ethyl-4′-aminopyrimidyl-(5′)]-methylformamino-5-hydroxy-Δ²-pentenyl-(3) alkyl disulfide (homothiamine alkyl disulfides). (I) can also be obtained by the reaction of alkyl mercaptan and oxidizing agent to (III) or by the reaction of (III) and alkyl thiocyanate, or by the application of two moles of hydrogen peroxide to the glacial acetic acid solution of dialkyl disulfide, and reacting thiamine to this solution at pH 8.