Amphiphilic Carbohydrate-Based Mesogens, 4 [1]. Synthesis of a Homologous Series of Mesogenic 1-O-n-Alkyl-D-mannitols

Regioselective reduction of a homologous series of O-n-hexyl to O-n-hexadecyl 2,3:5,6-bis-O-ethylboranediyl-β-D-mannofuranosides, la-k is achieved with ethyldiboranes(6) in the presence of 9-methanesulfonyloxy-9-borabicyclo[3.3.1] nonane [MSBBN]. After deboronation the mesogenic 1-O-n-alkyl-D-mannitols 2a-k are obtained, the liquid crystal ranges and solid state transitions of which are determined by D.S.C.