Abstract : A simple condensation reaction of thiocyanic acid with a ketohexose can provide a library of up to 10 different molecules composed of oxazolidinethiones (OZTs) or oxazolinethiones (OXTs). The question arising is “how to manage such a complex chemistry?” Careful control of the reaction conditions associated with purification sequences (involving selective protection or functionalization) can certainly help. A subtle and challenging chemical game could be played between selective pre- and post-protections and original functionalizing reactions. In this PhD work, we disclose the development of new chemical and purification tactics to access OZTs and oxazolidinones (OZOs) anchored onto ketohexose scaffolds, namely D-fructo and its epimers D-psico, D-tagato, whose chemistry has been poorly investigated in comparison with other monosaccharidic systems. Furthermore we have improved our understanding about saccharidic thionocarbamates chemistry for a better valorization from both chemical and biological point of view. We have generated a library of fixed tautomeric forms of hybrid compounds to be submitted to biological tests. This panel of compounds was subjected to antimicrobial screening and some molecules have shown very efficient effects. Moreover, the leading inhibitors of GLUT5 will be used in the development of biochemical tools for a better comprehension of the role of this D-fructose transporter in relation to type 2 diabetes and obesity.