Disaccharide Mimetics by Enzymatic Tandem Aldol Additions

Tail-to-tail C,C-coupled pyranoses or furanoses like 2 with a disaccharide-like structure were obtained from hydroxylated dialdehydes like 1 under aldolase catalysis. The key step is the twofold addition of dihydroxyacetone phosphate. As many as six stereocenters in the products can be controlled by a thermodynamically selective reaction mode.