Novel $alpha$,$ømega$-functionalized amphiphilic lipopolymers were prepared which are composed of a proximal transmembrane lipid moiety and a hydrophilic poly(2-oxazoline)-based (POx) polymer chain. The synthesis is started from bifunctional lipoinitiators which are asymmetrically protected as tert.butyldiphenylsilyl (TBDPS) ethers followed by cationic living ring-opening polymerization of 2-oxazolines in a one-pot multistep reaction. This results in polymers with defined terminal end groups and narrow molar mass distributions. All protective groups involved can be readily cleaved in a single step reaction keeping the structure of the polymer intact. This gives access to (lipo)polymers with a variety of defined identical or chemical orthogonal $alpha$,$ømega$-functionalities. The described synthetic strategy is a versatile tool for the preparation of defined polymer-drug or polymer-protein conjugates or asymmetric functionalized modeled lipid membranes for the quantitative study of membrane-associated phenomena such as transmembrane transport and cell adhesion / recognition.