Lipase mediated desymmetrization of meso 2,6-di(acetoxymethyl)-tetrahydropyran-4-one derivatives. An innovative route to enantiopure 2,4,6-trifunctionalized C-glycosides

Article abstract of DOI:10.1016/0957-4166(96)00380-1

The desymmetrization of several meso-configurated 2,4,6-trifunctionalized tetrahydropyrans was studied. Amongst the derivatives investigated the conformationally more rigid spiro ketal 8b afforded hydroxy-acetate (-)-12 in excellent chemical yield and enantiomeric excess. The absolute configuration of the resulting 2,4,6-trifunctionalized C-glycosides was established by X-ray crystal diffraction.