Reductive cleavage as a route to carbohydrate enolates. Applications to the synthesis of C-linked disaccharides

Abstract

The carbohydrate-derived α-bromo ketones 4 and 5undergo reductive cleavage using either Zn–Cu or CeCl3–Nal and the resulting enolates are trapped by carbohydrate-based aldehydes 6, 7 and 14 to give C-disaccharide derivatives.