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

[摘要]：The prepn. 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-temp. NMR expts. 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.

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