An efficient approach to the synthesis of CS disaccharide precursors programmed towards different natural sulfation patterns has been established. This divergent strategy enables access to protected CS-A, CS-C, CS-D, CS-E and CS-O derivatives from common disaccharide precursors. Optimisation of a central glycosylation reaction using shelf-stable thioglycoside D-Glc donors enables reproducible multigram scale synthesis with bstereoselectivity and ultimate access to D-GlcA(1,3-b)-D-GalN systems incorporating multiple orthogonal protecting groups. An exemplar synthesis of a free CS-C disaccharide is completed, containing an anomeric O-allyl handle, demonstrating capability for conjugation, for example using alkene click chemistry. Overall, this methodology offers an important contribution to provide the building blocks required for iterative CS oligosaccharide synthesis, for example using a [2+2] glycosylation approach and pre-programmed for regiospecific O-sulfation. The synthesis of longer, bespoke CS sequences for biological application is currently underway and will be reported in due course.