Facile Synthesis of 2-O-Iodoacetyl Protected Glycosyl Iodides: Useful Precursors of 1→2-Linked 1,2-trans-Glycosides

Abstract

The preparation and utilization of novel iodide glycosyl donors, 2-O-iodoacetyl-glycopyranosyl iodides, is described. The mechanism for the reaction of iodine with carbohydrate cyclic ketene acetal was investigated through low-temperature NMR experiments. 2-O-Iodoacetyl-glycopyranosyl iodides can serve as effective glycosyl donors giving 2-O-iodoacetyl 1,2-trans-glycosides in high yields and excellent stereoselectivities. The 2-O-iodoacetyl group was removed selectively with thiourea to afford 2-hydroxy 1,2-trans-glycosides in high yield without affecting other protecting groups and anomeric configurations.