Glycosyl diacylglycerols are excellent lipids for the formation of both bi- and monolayer lamellar systems but they are generally not commercially available, and the synthesis of optically pure glycosyl diacylglycerols inevitably involves protection and deprotection of glycerol linkers. A novel glycolipid designed to be an easily accessible structural surrogate of monoglucosyl diacylglycerol (MGDG) has been synthesized. Tn this molecule, glycerol is replaced with (S)-1,2,4-trihydroxybutane. Instead of the fatty acyl moieties found in MGDG, a 2,2-dialkyl-1,3-dioxolane function provides the hydrophobic moiety of the molecule. This different functionality affords chemically and physically tunable new properties in a glycolipid. These include base stability, increased mobility of the headgroup, possibilities of new packing arrangements, and the potential for use in encapsulation strategies using liposomes where a decrease in pH is used as the environmental cue for release, The acetal linkage also makes the molecule unsusceptible to degradation by phospholipase A and other esterase activities found in biological systems thus further extending their utility. The choice of the butane triol linker removes the common problem of racemization of protected glycerol by acetal and ester migration. It also affords synthetic simplicity since only one dioxolane acetal is formed on reaction of butane-1,2,4-triol with ketones, whereas in the case of glycerol, one hydroxyl group has to be selectively protected to avoid the formation of both enantiomers. 2-D NMR homonuclear and heteronuclear correlation spectroscopy together with nuclear Overhauser effect experiments and molecular mechanics calculation were used to obtain information on the headgroup orientation and on the configuration of the trialkoxybutane backbone. These supported a structure in which the alkyl chains were extended in a parallel fashion and the headgroup, although free to rotate along C2-C3 and C3-C4 of the trialkoxybutane substructure, extended away in the other direction in a manner similar to that observed in the case of MGDG. X-ray powder diffraction and optical microscopy data both supported a lamellar phase behavior of this amphiphilic molecule in water. H-1 NMR experiments monitoring the rate of acetal cleavage of this amphiphile revealed its tunable acid susceptibility. The unique structural feature, phase behavior, and controllable acid susceptibility of this glycolipid is potentially useful in many applications.