Efficient Glycosidation of a Phenyl Thiosialoside Donor with Diphenyl Sulfoxide and Triflic Anhydride in Dichloromethane

Abstract

The formation of sialic acid glycosides with a thiosialic acid derivative, diphenyl sulfoxide, and trifluoromethanesulfonic anhydride is reported. With an excess of diphenyl sulfoxide, glycal formation can be completely suppressed and excellent yields are obtained for coupling to a wide range of primary, secondary, and tertiary acceptors.