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Issue 43, 2017
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Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C6F5)3-catalyzed glycosylation of sterically-hindered precursors

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Abstract

A convergent synthesis of the complex, doubly-branched pentasaccharide domain of the natural-product immunoadjuvant jujuboside A is described. The key step is a sterically-hindered glycosylation reaction between a branched trisaccharide trichloroacetimidate glycosyl donor and a disaccharide glycosyl acceptor. Conventional Lewis acids (TMSOTf, BF3·Et2O) were ineffective in this glycosylation, but B(C6F5)3 catalyzed the reaction successfully. Inherent complete diastereoselectivity for the undesired α-anomer was overcome by rational optimization with a nitrile solvent system (1 : 5 t-BuCN/CF3Ph) to provide flexible, effective access to the β-linked pentasaccharide.

Graphical abstract: Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C6F5)3-catalyzed glycosylation of sterically-hindered precursors

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Publication details

The article was received on 10 Mar 2017, accepted on 04 May 2017 and first published on 04 May 2017


Article type: Communication
DOI: 10.1039/C7CC01783A
Citation: Chem. Commun., 2017,53, 5838-5841
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    Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C6F5)3-catalyzed glycosylation of sterically-hindered precursors

    R. R. Karimov, D. S. Tan and D. Y. Gin, Chem. Commun., 2017, 53, 5838
    DOI: 10.1039/C7CC01783A

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