Covering: up to November 2013. Heparin and heparan sulfate are natural polysaccharides with strong structural variations, which are responsible for their numerous specific biological properties. One key target of heparin, among others, is antithrombin, a serine protease inhibitor that, upon activation, mainly targets anticoagulation factors IIa and Xa. It is well documented that inhibition of the latter is due to a specific pentasaccharidic sequence, its synthetic analog being the registered drug fondaparinux. The replacement of hydroxyls by methoxy groups, N-sulfates by O-sulfonates and the modulation of the sulfation pattern gave rise to both idraparinux and its neutralizable form, idrabiotaparinux, two pentasaccharides with a significantly increased half-life compared to fondaparinux. Although numerous efforts have been devoted to improving the chemoenzymatic preparation of heparin fragments, enzymes are usually selective for their natural substrates, which limits the generation of some specific non-natural structures. Up to now, total synthesis has proved to be a valuable approach for the preparation of tailor-made and pure saccharides in the milligram to gram scale. This highlight will focus on the synthesis and the technical challenges associated with the development and the production of complex carbohydrates which will be exemplified with idrabiotaparinux. Particular attention will be paid to the process improvements needed in order to implement the production in a pilot plant, achieving batch generation on a multi-kilogram scale with a purity higher than 99.5%, and with no unknown impurity over 0.1%.