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Paper | Special issue | Vol 52, No. 3, 2000, pp.1203-1206
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S123
Perchloric Acid in 1,4-Dioxane and Perfluorooctanesulfonic Acid as Practical Catalysts for the Stereoselective Glycosylation of 1-O-Acetylglycosides

Yasuo Yokoyama, Takeshi Hanamoto, Xiu Lan Jin, Yong Zhi Jin, and Junji Inanaga*

*Institute for Fundamental Research of Organic Chemistry, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

Abstract

A perchioric acid solution in 1,4-dioxane and perfluorooctanesulfonic acid was found to be practical catalysts for the stereoselective glycosylation of 1-O-acetyiglycosides. Either the α- or β-anomer of the disaccharide, methyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzyl-D-ribofuranosyl)-α-D-glucopyranoside, was synthesized with complete stereoselectivities simply by changing the solvent. Epimerization of the kinetic product can effectively be suppressed in ether by the excess use of the polyoxygenated substrates.