Studies on the Pyrimidine Derivatives. XXX. Syntheses and Reactions of O-(2-Tetrahydropyranyl)-thiamine, O-Tritylthiamine, S-Acylthiamine, and S-Alkoxycarbonylthiamine.

Abstract

O-(2-Tetrahydropyranyl) thiamine (II) and O-tritylthiamine (III) were prepared from O-(2-tetrahydropyranyl) SB₁ (V) and O-trityl SB₁ (VII), respectively. II and III were converted into S-alkoxycarbonyl or S-acyl derivatives, and removal of the trityl group gave S-acylthiamine. S-Alkoxycarbonyl and S-acylthiamine reacted with phosgene to give O-chlorocarbonyl derivatives, which were converted into O-alkoxycarbonyl-and O-carbamoylthiamine. These compounds were also obtained from S-alkoxycarbonyl-and S-carbamoylthiamine by S→O rearrangement. The combination of these reactions gave various kinds of thiol type thiamine derivatives.