Collect. Czech. Chem. Commun.
2004, 69, 1768-1780
https://doi.org/10.1135/cccc20041768
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
Abstract
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.
