Synthesis of new cyclitol derivatives

Article abstract of DOI:10.1055/s-1997-1292

In recent years, an increasing interest in the synthesis of glycosidase inhibitors has been observed due to their biological properties. Glycosidase inhibitors can be classified in two distinct classes: reversible inhibitors (glycals, glyconolactones, glycosylamines, aminocyclitols, etc), and irreversible inhibitors (conduritol epoxides, 5,6-anhydro-1- deoxynojirimycine). Among the naturally occurring glycosidase inhibitors, cyclitol epoxides and aminocyclitols have been extensively studied due to their antibiotic properties. They have been synthesized from carbohydrate derivatives, endo-adducts of furan and acrylic acid or by chemoenzymatic conversion of aromatic derivatives. As part of our investigation on the synthesis of new potential enzyme inhibitors, we have recently prepared some new thiirane analogs. We also reported in a preliminary communication the synthesis of analogs of naturally occurring aminocyclitols. We now describe these previous results in further detail.