Phospholipids are a major component of all prokaryotic and eukaryotic membranes. The chemical structure of the phospholipid dictates the self-assembled bilayer structure formed as well as the membrane physical and mechanical properties. We are interested in the effect of vesicle structure and mechanical property when ribose is substituted for the conventional glycerol backbone. We have synthesized and characterized a series of carbohydrate-based lipids possessing chain lengths from C12 to C20. Structural and mechanical property studies indicate that below the phase transition, a lamellar crystalline phase is present and above the Tm, a fragile lamellar fluid state exists. Our results are likely to provide new insight for tailoring vesicle properties for pharmaceutical, cosmetic, and other industrial applications.