Step-by-step synthesis of monodisperse methacrylamidoalkyl oligolactates

This paper describes the facile step-by-step synthesis to graft lactic acid or lactoyl lactate onto primary as well as secondary alcohol derivatives of methacrylamides via esterification. Elongation of the chains is achieved by repeating the coupling reactions with either hydroxyl-protected monolactate or hydroxyl-protected dilactate, followed by mild deprotection using tetrabutylammonium fluoride. This versatile synthesis route generates, on a multigram scale, monodisperse oligolactates of predetermined lengths with functional end groups. The products can be used, for example, as building blocks for biodegradable polymeric materials.