Synthetic Applications of Cyclic Sulfites, Sulfates and Sulfamidates in Carbohydrate Chemistry

Abstract

Cyclic sulfites, sulfates and sulfamidates derived from saccharides have emerged as valuable and versatile synthons for the preparation of a wide variety of modified sugars and sugar related compounds owing to the combination of the easily and efficient forma- tion of these chemical sulfur derivatives from diols and aminoalcohols with the high chemical stability and enhanced reactivity of those functions towards nucleophiles. The state-of-the-art in this area is covered in the present review using the relative position of the diols and the aminoalcohol functions on the saccharide skeleton and the nature of the nucleophilic reagent (oxygenated nucleophiles, halogens, sulphur nucleophiles, nitrogen nucleophiles, and carbon nucleophiles) as expositive criteria. A comprehensive outlook of the applications of these sulfur derivatives in the preparation of compounds such as azido sugars, halo sugars, thiosugars, pseudo-saccharides, radiotrac- ers, enzymatic inhibitors, anticonvulsant agents, surfactants amongst others is also given.