2,3-UNSATURATED C-GLUCOPYRANOSIDES: A GUIDELINE TO THE ANOMERIC CONFIGURATIONAL ASSIGNMENT

Article abstract of DOI:10.1016/S0040-4039(00)80810-2

Contrary to a previous reporte, the SnCl4-pramoted arylation of tri-O-acetyl-D-glucal (1) by means of anisole (2) gives rise to 1'-(4,6-di-O-aceyl-2,3-dideoxy-β-D--erythro-hex-2-enopyranosyl)-4'-methoxybenzene (3) and not a-anamer (4).A quideline to the correct assignment of the anameric configuration of 2,3-unsaturated C-glucopyranosides is suggested, which violates the Hudson isorotation rule.