Two-dimensional (2D) materials are of great significance to the materials community as a result of their high surface area and controllable surface properties. However, controlled preparation of biodegradable 2D structures with biological activity is difficult. In this work we demonstrate that by careful selection of building block structures and assembly conditions it is possible to use crystallization-driven self-assembly (CDSA) to assemble well-defined 2D nanostructures from poly(l-lactide) (PLLA)-based diblock glycopolymers. 1D glyco-cylinders and 2D diamond-shaped glyco-platelets are produced, where the underlying formation mechanism is revealed by dissipative particle dynamics simulations. Furthermore, we demonstrate that assembly of the polymers under mild degradation provides a straightforward route to hollow-cored platelets, a morphology that has previously proven laborious to access. The well-defined sizes and shapes of the glyco-platelets allow us to investigate macrophage activation efficiency and demonstrate clear size and shape effects, pointing toward potential applications in immunology.