CARBOHYDRATES Polyfunctional Compounds in Nature

Because of the polyfunctional nature of carbohydrates, protective-group strategy plays an important role in synthetic methodology involving this class of compounds. In the present Chapter, results are described from a study of the utility of N-trimethylsilyl- and N-tert-butyldimethylsilyl-phthalimide for the selective silylation of primary hydroxyl groups in carbohydrates. Also described, is a new, facile method for cleavage of acetals and dithioacetals in carbohydrate derivatives the method involves treatment of the derivatives with a dilute solution of iodine in methanol. 

The complex and polyfunctional nature of carbohydrates has made the development of automated methods for oligosaccharide libraries extremely slow. However, carbohydrates can serve as excellent library scalfolds [27]. Several chiral hydroxyl groups, upon appropriate modifications and utilization, could be utilized further in the display of chemical diversities. This approach could provide a novel entry to different classes of compounds to be explored for drug-like properties. 

---