Amphiphilic and mesogenic carbohydrates. Part III: Synthesis and thermal behavior of di-O-(n-alkyl)-and tri-O-(n-alkyl)-D-glucose derivatives

The homologous series of the 2,3-di-O-(n-alkyl)-3a-e and 4,6-di-O-(n-alkyl)-D-glucopyranoses9a-e, as well as the 5,6-di-O-(n-hexadecyl)-D-glucofuranose15e, the 3,4,6-tri-O- and 1,4,6-tri-O-(n-octyl)-D-glucopyranoses10a and11a were prepared and their mesogenic properties studied. The derivatives3a-e and15e show enantiotropic but9a-e monotropic behavior. In contrast to this the bis single-tailed -D-glucosyl fluorides4e and7a and the tris single-tailed D-glucopyranoses10a and11a do not form any mesophase.