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Issue 27, 2019
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Gold(i)-promoted α-selective sialylation of glycosyl ortho-hexynylbenzoates for the latent-active synthesis of oligosialic acids

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Abstract

A gold(I)-promoted α-selective sialylation approach with 5-N,4-O-oxazolidinone-protected sialyl ortho-hexynylbenzoates as donors is described for the stereoselective synthesis of α-sialosides. Iterative couplings of the ‘active’ sialyl ortho-hexynylbenzoates and the ‘latent’ sialyl ortho-iodobenzoates provide a new approach for the ‘latent-active’ synthesis of α-(2 → 9)-linked oligosialic acids that are relevant to N. meningitidis serogroup C capsular polysaccharide.

Graphical abstract: Gold(i)-promoted α-selective sialylation of glycosyl ortho-hexynylbenzoates for the latent-active synthesis of oligosialic acids

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Publication details

The article was received on 26 Apr 2019, accepted on 19 Jun 2019 and first published on 19 Jun 2019


Article type: Communication
DOI: 10.1039/C9OB00954J
Org. Biomol. Chem., 2019,17, 6580-6584

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    Gold(I)-promoted α-selective sialylation of glycosyl ortho-hexynylbenzoates for the latent-active synthesis of oligosialic acids

    J. Wang, Q. Lou, J. Rong and Y. Yang, Org. Biomol. Chem., 2019, 17, 6580
    DOI: 10.1039/C9OB00954J

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