N ‐Acetyl‐5‐ N ,4‐ O ‐oxazolidinone‐Protected Sialyl Sulfoxide: An α‐Selective Sialyl Donor with Tf 2 O/(Tol) 2 SO in Dichloromethane | Zendy

Gu Zhenyuan | Zendy; Zhang Jiaxin | Zendy; Xing Guowen | Zendy

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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.

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