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Issue 30, 2013
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Highly efficient α-C-sialylation promoted by (p-Tol)2SO/Tf2O with N-acetyl-5-N,4-O-oxazolidione protected thiosialoside as donor

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Abstract

Based on a preactivation protocol with (p-Tol)2SO/Tf2O, a practical, straightforward, and high-yielding synthesis of α-sialyl C-glycosides was accomplished by coupling N-acetyl-5-N,4-O-oxazolidione protected thiosialoside with various trimethylsilyl enol ethers and allyltrimethylsilanes. High yields and excellent α-selectivities were obtained for the strong π-nucleophiles with large nucleophilicity values (N = 4.4–9.0), irrespective of whether silyl enol ethers, silyl ketene acetals or allyltrimethylsilanes were used for the electrophilic C-sialylation.

Graphical abstract: Highly efficient α-C-sialylation promoted by (p-Tol)2SO/Tf2O with N-acetyl-5-N,4-O-oxazolidione protected thiosialoside as donor

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Publication details

The article was received on 28 Apr 2013, accepted on 10 Jun 2013 and first published on 10 Jun 2013


Article type: Paper
DOI: 10.1039/C3OB40876K
Citation: Org. Biomol. Chem., 2013,11, 5017-5022
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    Highly efficient α-C-sialylation promoted by (p-Tol)2SO/Tf2O with N-acetyl-5-N,4-O-oxazolidione protected thiosialoside as donor

    Z. Gu, X. Zhang, J. Zhang and G. Xing, Org. Biomol. Chem., 2013, 11, 5017
    DOI: 10.1039/C3OB40876K

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