Sapporo Medical Journal

Abstract : In this study, new glycolipids derivatives have been synthesized by modification of the head group. The glycosylation reaction was perform using monosaccharide pentacetates with n-dodecanol in presence of borontriflouride. After deacetylation under basic medium, the benzylidene protecting on 4 and 6 hydroxyls on sugar follow by introducing of two propargylic group on remaining hydroxyls on 2 and 3 positions. The click reaction of sodium azide provide two triazole rings on the final structures of glycolipids 6 and 7. The liquid crystalline phases of the materials were investigated extensively by optical polarized macroscope (POM), and differential scan calorimetry (DSC). The thermotropic behavior of these glycolipids reveal the formation of lamellar phase at the range of 60-70 oC. While the lyotropic under penetration of water reveal a cubic phase for 6 and bi-continues cubic phase for 7. All the compounds was characterized by nuclear magnetic resonance spectroscopy (1H and 13CNMR), Fourier transform infrared spectroscopy (FTIR) and mass spectrometry (MS).