Regio- and Stereocontrolled Synthesis of 2d-Deoxy Lewisx Pentasaccharide

Authors

  • Yanyan Zhang,

    1. Université Pierre et Marie Curie-Paris 6, Institut Parisien de Chimie Moléculaire, UMR 7201 CNRS, 4 place Jussieu, 75005 Paris, France, Fax: +33-1-44275504
    2. Guiyang College of Traditional Chinese Medicine, 50 Shidong Road, 550002 Guiyang, China
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  • Dengxiang Dong,

    1. Université Pierre et Marie Curie-Paris 6, Institut Parisien de Chimie Moléculaire, UMR 7201 CNRS, 4 place Jussieu, 75005 Paris, France, Fax: +33-1-44275504
    2. Guiyang College of Traditional Chinese Medicine, 50 Shidong Road, 550002 Guiyang, China
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  • Huanhuan Qu,

    1. Université Pierre et Marie Curie-Paris 6, Institut Parisien de Chimie Moléculaire, UMR 7201 CNRS, 4 place Jussieu, 75005 Paris, France, Fax: +33-1-44275504
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  • Matthieu Sollogoub,

    1. Université Pierre et Marie Curie-Paris 6, Institut Parisien de Chimie Moléculaire, UMR 7201 CNRS, 4 place Jussieu, 75005 Paris, France, Fax: +33-1-44275504
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  • Yongmin Zhang

    1. Université Pierre et Marie Curie-Paris 6, Institut Parisien de Chimie Moléculaire, UMR 7201 CNRS, 4 place Jussieu, 75005 Paris, France, Fax: +33-1-44275504
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Abstract

The total synthesis of 2d-deoxy Lewisx pentasaccharide is described. Ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α,β-D-galactopyranoside was condensed with a diol of glucosamine to regio- and stereoselectively give the disaccharide, the C-2′ position was then reduced after stereoselective fucosylation to afford a Lewisx trisaccharide analogue. Regioselective glycosylation of a known lactoside diol with this trisaccharide provided a pentasaccharide that, after deprotection, gave the target pentasaccharide.

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