For the synthesis of some azido-and aminocyclitols, (3aRS, 7aSR)-1,3,3a,7a-tetrahydroisobenzofuran was used as the starting material. For further functionalization of the diene unit, the diene was subjected to epoxidation reactions to give mono-and bisepoxides depending on the amount of m-chloroperbenzoic acid used. The ring-opening of the epoxide functionality with NaN3 resulted in the formation of mono- and bisazido cyclitols. The tetrahydrofuran ring was opened in an acid-catalysed reaction with sulfamic acid. The reduction of azide groups to give amines provided various amino-and bisaminocyclitol derivatives. The inhibitory effects of 20 compounds against alpha-glucosidase and alpha-amylase were tested. The results indicated that some of these compounds seem to have good inhibitory activity against alpha-glucosidase, and low inhibitory activity against alpha-amylase. Furthermore, it was demonstrated that the number and position of azides, amines, and hydroxy groups appeared to play an important role in determining the inhibitory potency of these compounds.