Collect. Czech. Chem. Commun. 2004, 69, 1768-1780

Synthesis of a (1→3)-Linked α-L-Fucose Tetrasaccharide

Michael Ludewig and Joachim Thiem*

Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany


Orthoester-protected benzyl and methyl 1-thiofucopyranosides could be opened to give fucopyranosides unblocked at position 3. Convergent glycosylations of such donors and acceptors led to the corresponding disaccharides, and their block condensation could be elaborated to give the (1→3)-linked α-L-fucose tetrasaccharide. Compounds of this structure are of interest with regard to the role of fucose in metastasis development in lung tissue.

Keywords: Fucose; Orthoesters; Thioglycosides; Oligosaccharides; Carbohydrates; α,(1→3)-Fucose tetrasaccharide; Glycosidations.

References: 22 live references.