S-(α-Acyloxyalkyl)thiamine誘導体の合成 : ビタミンB_1および諸関係化合物の研究(CVIII)

概要

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Some attemps were made to synthesize S-(α-acyloxyalkyl) thiamine derivatives expecting thiamine activity. S-Alkylthiamines were oxidized with hydrogen peroxide in acetic acid to afford S-alkylthiamine sulfoxides (V-VII). The sulfoxides were found to be very inert to the attempted Pummerer rearrangement under ordinary conditions. Thus treatments of them with acetic anhydride gave S-alkyl-O-acetylthiamine sulfoxides (VIII, IX) under room temperature and S-alkyl-O, N-diacetylthiamine sulfoxides (X, XI) at 50-70℃. Treatments of V and VI, however, with acetic anhydride under more severe conditions, at 100-120℃, they underwent Pummerer rearangement to give XIII and XIV in poor yields. Some other S-(α-acyloxyalkyl) thiamine derivatives (XV-XVII) were also obtained by the reaction of the thiol-form salt of thiamine and l-benzoyloxyalkylchloride. All these derivatives (XIII-XVII) were found to be easily hydrolyzed to thiamine with hydrochloric acid and to show thiamine activities in rats.
日本ビタミン学会の論文
1969-05-25