Synthesis and properties of some α-D-alkyl glucosides and mannosides: apparent molal volumes and solubilization of nitrobenzene in water at 25 °C

Abstract

Normal and cyclic α-D-alkyl glucosides and mannosides have been synthesized in a one-step procedure from the corresponding sugar. The apparent molal volume and the influence on the solubility of nitrobenzene of some of these glycosides have been measured in water at 25 °C. Evidence for micelle formation is presented for α-D-n-hexyl glucoside, -n-octyl glucoside, and -cyclohexyl mannoside. Comparison of the physical properties of the aqueous solutions shows that the stereochemistry of the sugar unit plays an important role in the hydrophobic hydration and hydrophobic interactions of the glycosides.