Synthesis of some 1-substituted 5,5-diethoxy-2,2-(propyl-1,3-disulfanyl)pentane-1,4-diols from 1,1-diethoxy-3-(1,3-dithian-2-yl)-propan-2-ol
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The starting material for this investigation was 3,3,4,4-tetraethoxybut-1-yne (TEB). This compound is highly functionalized as it contains a triple bond, a protected ketone, and a protected aldehyde, and can undergo a variety of different reactions. The aim of this project was to synthesize 1-substituted 5,5-diethoxy-2,2-(propyl-1,3-disulfanyl)pentane-1,4-diols from 1,1-diethoxy-3-(1,3-dithian-2-yl)propan-2-ol. These compounds are valuable as they can undergo further reactions to form modified carbohydrate analogues, a class of compounds of great interest for the development of new drugs. The target compounds were synthesized in moderate to excellent yields using n-butyllithium and aldehyde or ketone as reactants. Two of the compounds were also synthesized by first using sodium hydride instead of one of the two equivalents of n-butyllithium. This method gave low to moderate yields. The target compounds have previously been synthesized, but by a different route, and these compounds have further been reacted to form carbohydrate analogues by deprotection of the dithiane moiety and subsequent cyclization. The conversion of 1,1-diethoxy-3-(1,3-dithian-2-yl)propan-2-ol into 1-substituted 5,5-diethoxy-2,2-(propyl-1,3-disulfanyl)pentane-1,4-diols makes it possible to synthesize the same carbohydrate analogues by a new route involving fewer steps and introducing the different substituents at a later stage in the synthetic route. Based on the results obtained in this thesis, further work has been suggested.
PublisherThe University of Bergen
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