Efficient dehydrative sialylation of C-4-aminated sialyl-hemiketal donors with Ph2SO/Tf2O.
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.
Ye
Deju
D
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.
Liu
Wenfeng
W
Zhang
Dengyou
D
Feng
Enguang
E
Jiang
Hualiang
H
Liu
Hong
H
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
D000588:Amines; D001555:Benzene Derivatives; D008698:Mesylates; D011743:Pyrimidines; C048860:diphenyl sulfoxide; D019158:N-Acetylneuraminic Acid; C012077:trifluoromethanesulfonic acid; C030986:pyrimidine