C-1 LITHIATION OF C-2 ACTIVATED GLUCALS

Article abstract of DOI:10.1016/S0040-4039(00)96921-1

Direct lithiation of the readily available 2-benzyloxy and the 2-phenylthio glucals 1 and 7 at the anomeric carbon atom leads to intermediates reacting with different electrophiles.Subsequent removal of the phenylthio group in compounds 9a, b with Raney-nickel and distereospecific 1-hydrogen- and 2-hydroxy-transfer with the BH3*SMe2/H2O2, NaOH system provides a convenient entry into functionalized C-glucopyranosides.