• TLC-MS
• LC-MS
• HPLC
• Carbohydrates
• Synthesis
• Organic
• Glycosidase
• Cyclitol
• Carbasugar
• NMR
• Warhead
• Inhibition

This work illustrates an efficient method for orthogonal protection of hydroxyl groups in the synthesis of a cyclitol derivative. The application of this synthetic pathway may lead to defining new inhibitors for a wide class of enzyme, exo- and endoglycosidases, and could potentially be used in the construction of new active molecules. Efficient synthetic methodologies are needed to fully capitalize on this promising class of putative covalent inhibitors. Special emphasis was given to the definition of a protection scheme that allowed the execution of stereo-selective reactions with satisfactory yields (11% over 14 steps), and to the optimization of the nine purification steps. The methods herein described were also applied to a wide range of scales showing consistency in the yields.