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