ピリミジン誘導体および関連化合物の研究(第43報) : O, S-Bis-(ethoxycarbonyl)thiamineの1新全合成法

概要

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A very convenient route to obtain DCET (III) via B_1 acetal was presented. 3-Acetyl-3- chloropropanol (VI) was converted into O-tetrahydropyranyl acetal (VII) and condensed with dithiocarbamic acid (IX) to give thiazolidinethione acetal (X) readily. Dehydration of X by SoCl_2-pyridine gave SB_1 acetal (XV) in a high yield. Oxidative desulfurization of XV in AcOH solution in the presence of AcONa afforded B_1 acetal (XIV), which was easily separated as thiocyanate. XIV reacted with ClCOOC_2H_5 in NaOH solution to give CET acetal (XVII) in a high yield, and DCET was readily obtained from XVII by thd action of phosgene with subsequent treatment with ethanol. This method is considered to be very convenient in producing DCET industrially, because each step progresses by simple operation and in a high yield.
公益社団法人日本薬学会の論文
1967-03-25