• disaccharides
• PTP1B ligands
• stereoselectivity

Carbohydrates represent one of the most abundant classes of biomolecules found in living organisms. Oligosaccharides,in particular, require multi-step chemical synthetic strategie due to the dense concentration of stereocentres and hydroxyl groups. Our research group has found a new one-pot microwave-activated reiterative assembly of glycal-derived vinyl epoxides in an uncatalyzed substrate-dependent stereospecific process. We have also started to create a library of oligosaccharides, that focusing on the inhibitor of PTP1B. PTP1B is a member of the protein tyrosine phosphatase (PTP) family, which is involved in a lot of cellular mechanisms and in the pathogenesis of several human diseases including metabolic disorders and neurodegenerative diseases. The aim of my thesis work is the synthesis of new stereodefined 2,3-unsaturated disaccharides as ligands for PTP1B. I have also optimized synthesis and purification protocol of the two major active compounds tested. To expand the molecular library, we focused on the synthesis of disaccharide with alkyl amino chains, given the affinity, reported in the literature of trodusquemine, which has a specific alkylamino chain, identified as spermine. This natural molecule is an allosteric inhibitor of PTP1B and shown neuroprotective effects in preclinical models of Alzheimer disease. To obtain the final products it was necessary to finely tune a deprotection reaction of these disaccharides.