title: N-acetyl-5-N,4-O-oxazolidinone-protected sialyl sulfoxide: an α-selective sialyl donor with Tf2O/(Tol)2SO in dichloromethane.
abstract: Sweet as sugar: Sialyl sulfoxide protected by N-acetyl-5-N,4-O-oxazolidinone was readily prepared, and its coupling to various sugar acceptors was investigated. When the reaction was promoted by Tf(2)O/(Tol)(2)SO, efficient and highly α-selective sialylation yielded α(2,6), α(2,3), and α(2,4) glycosidic linkages between sialic acid and glucose/glacotose.
authors.affiliation: Department of Chemistry, Beijing Normal University, Beijing 100875, China.
authors.forename: Zhen-yuan
authors.initials: ZY
authors.lastname: Gu
authors.forename: Jia-xin
authors.initials: JX
authors.lastname: Zhang
authors.forename: Guo-wen
authors.initials: GW
authors.lastname: Xing
mesh_terms: D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D005690:Galactose / Q000138:chemical synthesis / Q000737:chemistry; D005947:Glucose / Q000138:chemical synthesis / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D008752:Methylene Chloride / Q000737:chemistry*; D019158:N-Acetylneuraminic Acid / Q000138:chemical synthesis / Q000737:chemistry*; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000737:chemistry*; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry*; D013454:Sulfoxides / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D005663:Furans; D006001:Glycoconjugates; D023303:Oxazolidinones; D013449:Sulfonamides; D013454:Sulfoxides; D008752:Methylene Chloride; C474725:triflic anhydride; D019158:N-Acetylneuraminic Acid; D005947:Glucose; D005690:Galactose