title: Efficient dehydrative sialylation of C-4-aminated sialyl-hemiketal donors with Ph2SO/Tf2O.
abstract: An efficient approach to the dehydrative sialylation of various substrates with C-4-aminated sialyl-hemiketal donors by using the reagent combination of diphenyl sulfoxide and triflic anhydride is reported. By using a C-4-hindered non-nucleophilic amine auxiliary, excellent yields and high alpha-stereoselectivities were obtained for coupling with a wide range of primary and secondary acceptors.
authors.affiliation: The Center for Drug Discovery and Design, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.
authors.forename: Deju
authors.initials: D
authors.lastname: Ye
authors.forename: Wenfeng
authors.initials: W
authors.lastname: Liu
authors.forename: Dengyou
authors.initials: D
authors.lastname: Zhang
authors.forename: Enguang
authors.initials: E
authors.lastname: Feng
authors.forename: Hualiang
authors.initials: H
authors.lastname: Jiang
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
mesh_terms: D000107:Acetylation; D000588:Amines / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000588:Amines; D001555:Benzene Derivatives; D008698:Mesylates; D011743:Pyrimidines; C048860:diphenyl sulfoxide; D019158:N-Acetylneuraminic Acid; C012077:trifluoromethanesulfonic acid; C030986:pyrimidine