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Org Biomol Chem. 2013 Aug 14;11(30):5017-22. doi: 10.1039/c3ob40876k. Epub 2013 Jun 25.

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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1
Department of Chemistry, Beijing Normal University, Beijing 100875, China.

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.

PMID:
23799610
DOI:
10.1039/c3ob40876k
[Indexed for MEDLINE]
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