The use of Carbohydrates in the Synthesis and Configurational Assignments of Optically Active, Non-Carbohydrate Compounds

Abstract

This chapter illustrates the practical applications of carbohydrates in asymmetric synthesis. The chapter also describes the application of carbohydrates for the synthesis and configurational proof of other biologically important molecules. Carbohydrates provide excellent chiral frameworks for mechanistic studies of asymmetric synthesis and serve as readily available and easily modified sources of asymmetric centers. The main essence of asymmetric synthesis is the creation of asymmetric centers under the influence of other asymmetric centers, in such a way that the resulting enantiomers or diastereoisomers are formed in unequal proportions. Asymmetric reactions can be divided into three types—namely, type 1 reactions in which optically active compounds are formed from achiral substrates and chiral reagents, or from achiral substrates and achiral reagents in chiral solvents, type 2 reactions in which new asymmetric centers are created in molecules that already possess one asymmetric center or more and in which the new asymmetric center may be liberated from the parent molecule by simple hydrolytic reactions, and type 3 reactions in which new asymmetric centers are created immediately adjacent to existing asymmetric centers in molecules that contain one asymmetric center.