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Synthesis of 3″- and 4″-deoxy-Lewisx trisaccharides: A useful tool for study of carbohydrate-carbohydrate interaction

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Abstract

Synthesis of 3″-deoxy and 4″-deoxy Lewisx trisaccharides is described. Phenyl 2,3,6-tri-O-benzoyl-4-deoxy-1-thio-β-d-xylo-hexopyranoside was condensed with a diol of glucosamine to give regio- and stereo-selectively a disaccharide. Stereoselective fucosylation of this disaccharide provided a protected deoxy Lewisx trisaccharide which was deprotected to give the 4″-deoxy Lewisx trisaccharide. Application of the similar synthetic sequence provided the 3″-deoxy Lewisx trisaccharide.

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Authors and Affiliations

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

    DengXiang Dong, Chafika Gourmala, YanYan Zhang & YongMin Zhang

  2. Guiyang College of Traditional Chinese Medicine, Guiyang, 55000250, Shidong Road, China

    DengXiang Dong, YanYan Zhang & YongMin Zhang

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  1. DengXiang Dong
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  2. Chafika Gourmala
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  3. YanYan Zhang
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  4. YongMin Zhang
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Correspondence to YongMin Zhang.

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Dong, D., Gourmala, C., Zhang, Y. et al. Synthesis of 3″- and 4″-deoxy-Lewisx trisaccharides: A useful tool for study of carbohydrate-carbohydrate interaction. Sci. China Chem. 53, 1963–1969 (2010). https://doi.org/10.1007/s11426-010-4060-6

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  • DOI: https://doi.org/10.1007/s11426-010-4060-6

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