Study of carbohydrate-carbohydrate interactions: total synthesis of 6d-deoxy Lewis pentaosyl glycosphingolipid |
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Authors: | Yanyan Zhang Dengxiang Dong Tao Zhou Yongmin Zhang |
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Institution: | a Université Pierre et Marie Curie-Paris 6, Institut Parisien de Chimie Moléculaire, UMR 7201 CNRS, 4 place Jussieu, 75005 Paris, France b Guiyang College of Traditional Chinese Medicine, 50 Shidong Road, 550002 Guiyang, China |
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Abstract: | This article describes total synthesis of 6d-deoxy Lewisx pentaosyl glycosphingolipid, a useful tool for study of the Lewisx-Lewisx interaction. A 6-deoxy galactose donor was condensed with a diol of glucosamine to provide regioselectively a β 1→4 linked disaccharide, which was further fucosylated to a protected deoxy Lewisx trisaccharide. Glycosylation of a lactoside diol with the 6d-deoxy Lewisx trisaccharide gave regio- and stereoselectively a pentasaccharide in excellent yield. After chemical modification, this pentasaccharide reacted with the 3-O-benzoylated azidosphingosine to form a glycosphingolipid, which, after azide reduction followed by condensation with stearic acid and deprotection, afforded the target compound. |
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Keywords: | Synthesis Glycosylation Carbohydrate-carbohydrate interaction Lewisx Glycosphingolipid |
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