title: 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.
authors.affiliation: National Center for Inter-University Research Facilities, Seoul National University, Seoul, 151-747, Korea.
authors.forename: Yoon-Joo
authors.initials: YJ
authors.lastname: Ko
authors.forename: Seung-Bo
authors.initials: SB
authors.lastname: Shim
authors.forename: Jung-Hyu
authors.initials: JH
authors.lastname: Shin
mesh_terms: D020650:Combinatorial Chemistry Techniques; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D006847:Hydrocarbons, Iodinated