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Disaccharide Mimetics by Enzymatic Tandem Aldol Additions

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  • Enzymes in Organic Synthesis, Part 10. This work was supported by the Deutsche Forschungsgemeinschaft (Grant Fe244/2–2) and the Schwerpunkts-programm “Synthese-Enzyme” from the state of Baden–Württemberg. We thank Christina Schütte for experimental assistance. Part 9: [5].

  • Dedicated to Professor R. R. Schmidt on the occasion of his 60th birthday

Abstract

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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.

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