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Paper | Regular issue | Vol 81, No. 11, 2010, pp.2569-2580
Published online, 10th September, 2010
DOI: 10.3987/COM-10-12043
Convertible Formation of Different Glycoside Using Molecular Iodine

Rungnapha Saeeng,* Uthaiwan Sirion, Yada Sirichan, Thanida Trakulsujaritchok, and Poolsak Sahakitpichan

*Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi 20131, Thailand


The observation of convertible formation between 2-deoxy-2-iodo-O-glycosides and 2,3-unsaturated glycoside was described. The selective formation of 2-deoxy-2-iodo-O-glycosides was found from the reaction of D-glucal with iodine in the excess alcohol acceptor or the addition of ceric ammonium nitrate as additive while the addition of a stoichiometric amount of alcohol in solvent favored 2,3-unsaturated glycosides formation.