The synthesis of alpha,omega-hydroxy telechelic, low-molecular-weight oligomers (degree of polymerization of less than 10) of glycidyl nitrate (GLYN) and 3,3-(nitratomethyl) methyl oxetane (NIMMO) by the activated monomer mechanism is described. Difunctional and/or trifunctional compounds may be prepared. The end-nitration of these compounds has been investigated using dinitrogen pentoxide in dichloromethane to form alpha,omega-nitrato telechelic oligomers. The materials were characterized by size exclusion chromatography, infrared and nuclear magnetic resonance spectroscopies. Differential scanning calorimetry was used to study the thermal properties of the compounds as they are envisaged to be energetic and fully compatible (miscible) plasticizers for the new generation of energetic binders such as polyNIMMO or polyGLYN, in propellant and explosive applications.