Straightforward synthesis of cholesterol functionalized aliphatic N-substituted 8 membered cyclic carbonate (Chol-8m) monomer is reported. Well-defined poly(ethylene glycol) (PEG) diblock copolymers were readily accessed via organo catalytic ring opening polymerization. These polymers show promise as building blocks for self-assembled nanostructures and steric stabilizers for liposomes.