1167429-99-3Relevant academic research and scientific papers
Highly regioselective oxirane ring-opening of a versatile epoxypyrrolidine precursor of new imino-sugar-based sphingolipid mimics
Rives, Arnaud,Genisson, Yves,Faugeroux, Vanessa,Zedde, Chantal,Lepetit, Christine,Chauvin, Remi,Saffon, Nathalie,Andrieu-Abadie, Nathalie,Colie, Sandra,Levade, Thierry,Baltas, Michel
experimental part, p. 2474 - 2489 (2009/09/29)
An in-depth study of the oxirane ring-opening reaction of a pivotal epoxypyrrolidine is reported. The introduction of various carbon- and heteroatom-centered nucleophiles at C4 has been achieved with high regiocontrol. The structures of the major products were assigned on the basis on an X-ray crystallographic study of six examples. A mechanistic study carried out at the B3LYP/6-31G** level of theory suggested that the steric control of the vinyl substituent was responsible for the regioselectivity. Finally, this approach was used to design and prepare imino-sugar-based sphingolipid mimics. A highly cytotoxic C-octylpyrrolidine is described. This compound was shown to interfere with the metabolism of sphing-olipids in murine melanoma cells, notably in inhibiting the production of glucosylceramide. Wiley-VCH Verlag GmbH & Co. KGaA.
