Premium
N ‐Acetyl‐5‐ N ,4‐ O ‐oxazolidinone‐Protected Sialyl Sulfoxide: An α‐Selective Sialyl Donor with Tf 2 O/(Tol) 2 SO in Dichloromethane
Author(s) -
Gu Zhenyuan,
Zhang Jiaxin,
Xing Guowen
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200172
Subject(s) - sialic acid , chemistry , glycosidic bond , sulfoxide , sugar , dimethyl sulfoxide , stereochemistry , biochemistry , organic chemistry , enzyme
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.