A stereodivergent approach for producing piperidine iminosugars has been developed employing a common optically active precursor. The key steps of the synthetic pathway are the double diastereoselection in the asymmetric dihydroxylation of the suitable chiral vinyl epoxy ester and the regio- and stereospecific opening of the epoxide ring with azide. The synthesis of two piperidine iminosugars, 1-deoxy-D-altronojirimycin and 1-deoxy-D-nojirimycin, was achieved by two related routes.
Stereodivergent synthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin
Primitivo L;Mencarelli P;Ricelli A;
2021
Abstract
A stereodivergent approach for producing piperidine iminosugars has been developed employing a common optically active precursor. The key steps of the synthetic pathway are the double diastereoselection in the asymmetric dihydroxylation of the suitable chiral vinyl epoxy ester and the regio- and stereospecific opening of the epoxide ring with azide. The synthesis of two piperidine iminosugars, 1-deoxy-D-altronojirimycin and 1-deoxy-D-nojirimycin, was achieved by two related routes.File in questo prodotto:
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