Synthesis of alpha- and beta-C-Aryl Delta(2)-Glycopyranosides from p-tert-Butylphenyl Delta(2)-Glycopyranosides via Grignard Reagents.

Treatment of p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-alpha-D-erythro-hex-2-enopyranoside (1aalpha) or the 4,6-di-O-(tert-butyldimethylsilyl) analogue (1balpha) with various functionalized arylmagnesium bromides in the presence of a catalytic amount of PdCl(2)(dppf) at 25 degrees C in THF afforded the corresponding unsaturated C-arylglycosides 2-14… CONTINUE READING