Synthesis of Specifically Fluorinated Methyl β-Glycosides of (1→6)-β-D-Galactooligosaccharides II. Methyl 4-Deoxy-4-fluoro-6-O-(β-D-galactopyranosyl)-β-D-galactopyranoside

Publisher Website
Google Scholar
Abstract
Condensation of methyl 2,3-di-O-benzyl-4-deoxy-4-fluoro-.beta.-D-galactopyranoside with 2,3,4,6-tetra-O-acetyl-.alpha.-D-galactopyranosyl bromide in the presence of mercuric cyanide in benzene afforded, in excellent yield, the .beta.-linked product. Its deblocking, effected by hydrogenolytic cleavage of the benzyl groups followed by deacetylation or, alternatively, via a pathway where the sequence of the deblocking reactions was reversed, gave crystalline title disaccharide 10. The structures of the compounds involved in the synthesis were confirmed by 13C NMR spectroscopy.