Efficient glycosidation of a phenyl thiosialoside donor with diphenyl sulfoxide and triflic anhydride in dichloromethane.
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.
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
David
D
Crich
Wenju
W
Li
D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D008752:Methylene Chloride / Q000737:chemistry*; D015394:Molecular Structure; D012794:Sialic Acids / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry*
D001555:Benzene Derivatives; D005663:Furans; D006027:Glycosides; D012794:Sialic Acids; D013449:Sulfonamides; C048860:diphenyl sulfoxide; D008752:Methylene Chloride; C474725:triflic anhydride