AMPHIPHILIC AND MESOGENIC CARBOHYDRATES .3. SYNTHESIS AND THERMAL-BEHAVIOR OF DI-O-(N-ALKYL)-D-GLUCOSE 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-glucopyranoses 9a-e, as well as the 5,6-di-O-(n-hexadecyl)-D-glucofuranose 15e, the 3,4,6-tri-O- and 1,4,6-tri-O-(n-octyl)-D-glucopyranoses 10a and 11a were prepared and their mesogenic properties studied. The derivatives 3a-e and 15e show enantiotropic but 9a-e monotropic behavior. In contrast to this the '' bis single-tailed'' alpha-D-glucosyl fluorides 4e and 7a and the ''tris single-tailed'' D-glucopyranoses 10a and 11a do not form any mesophase.