Facile synthesis of 2-O-iodoacetyl protected glycosyl iodides: useful precursors of 1-->2-linked 1,2-trans-glycosides.
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.
Ko
Yoon-Joo
YJ
National Center for Inter-University Research Facilities, Seoul National University, Seoul, 151-747, Korea.
Shim
Seung-Bo
SB
Shin
Jung-Hyu
JH
D020650:Combinatorial Chemistry Techniques; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D006027:Glycosides; D006847:Hydrocarbons, Iodinated