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 / De Angelis, M.; Sappino, C.; Mandic, E.; D'Alessio, M.; De Dominicis, M. G.; Sannino, S.; Primitivo, L.; Mencarelli, P.; Ricelli, A.; Righi, G.. - In: TETRAHEDRON. - ISSN 0040-4020. - 79:(2021), pp. 1-9. [10.1016/j.tet.2020.131837]
Stereodivergent synthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin
De Angelis M.
Primo
;Sappino C.;D'Alessio M.;Sannino S.;Primitivo L.;Mencarelli P.;
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 | Dimensione | Formato | |
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