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Issue 4, 2014
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Efficient synthesis of a library of heparin tri- and tetrasaccharides relevant to the substrate of heparanase

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Abstract

The glycosylation reaction for construction of the challenging α-GlcN–(1→4)-GlcA/IdoA linkages has been investigated carefully. A standard protocol was thus fixed that employed 2-azido-glucopyranosyl N-phenyl trifluoroacetimidates as donors, TMSOTf as a catalyst, toluene as a solvent, and −30 °C as the working temperature. With this protocol, a variety of mono- and disaccharide donors and acceptors were condensed reliably to provide the corresponding coupled tri- and tetrasaccharides in satisfactory yields and α-selectivity, whereas a remote protecting group or a sugar unit in either the donor or the acceptor did affect considerably the outcome. The resulting tri- and tetrasaccharides bearing orthogonal protecting groups were then converted efficiently into the corresponding heparin tri- and tetrasaccharides via a robust approach involving saponification, O-sulfation, azide reduction, N-sulfation/N-acetylation, and global debenzylation. These heparin tri- and tetrasaccharides are structurally relevant to ΔHexA(2S)–GlcN(NS,6S)–GlcA–GlcN(NS,6S), a reported substrate of heparanase, and therefore could be exploited to examine the substrate specificity of this important enzyme.

Graphical abstract: Efficient synthesis of a library of heparin tri- and tetrasaccharides relevant to the substrate of heparanase

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Publication details

The article was received on 11 Feb 2014, accepted on 20 Mar 2014 and first published on 21 Mar 2014


Article type: Research Article
DOI: 10.1039/C4QO00039K
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Citation: Org. Chem. Front., 2014,1, 405-414
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    Efficient synthesis of a library of heparin tri- and tetrasaccharides relevant to the substrate of heparanase

    P. Xu, W. Xu, Y. Dai, Y. Yang and B. Yu, Org. Chem. Front., 2014, 1, 405
    DOI: 10.1039/C4QO00039K

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