Synthesis of fucosyl saccharides under neutral conditions in solutions of 
lithium perchlorate in dichloromethane

Schmid, U; Waldmann, Herbert

doi:10.1002/(SICI)1521-3765(19980310)4:3<494::AID-CHEM494>3.0.CO;2-8

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Synthesis of fucosyl saccharides under neutral conditions in solutions of lithium perchlorate in dichloromethane

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Waldmann, Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Citation

Schmid, U., & Waldmann, H. (1998). Synthesis of fucosyl saccharides under neutral conditions in solutions of lithium perchlorate in dichloromethane. CHEMISTRY-A EUROPEAN JOURNAL, 4(3), 494-501. doi:10.1002/(SICI)1521-3765(19980310)4:3<494:AID-CHEM494>3.0.CO;2-8.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-9CB5-C

Abstract

Trisaccharides embodying the Fuc-alpha-(1-2)-Gal or the Fuc-alpha-(1-2)-Glc substructure can be built up under neutral conditions by glycosylation of selectively deprotected glycosyl acceptor disaccharides with 2,3,4-tri-O-benzyl fucosyl fluoride in 0.07 M solutions of LiClO4 in CH2Cl2. The glycosyl and the galactosyl trisaccharides, which are stereoisomers of the carbohydrate determinant of the human blood group H, are obtained in high yield and with complete alpha-selectivity. The glycosyl acceptor disaccharides with a deblocked 2-OH group in the saccharide unit are obtained by treatment of the respective 1,2-anhydro carbohydrates with glycosyl acceptors in 0.07 M LiClO4/CH2Cl2.