Synthesis of beta-L-fucopyranosyl phosphate and L-fucofuranosyl phosphates by the MacDonald procedure.
Fusion of beta-L-fucopyranose tetraacetate with phosphoric acid for 1 min at 50 degrees gives a 9:1 anomeric mixture of the alpha- and beta-pyranosyl phosphates. Longer fusion times give the alpha-anomer exclusively. The L-fucofuranose tetraacetates were synthesized for the first time by acetolysis of methyl-2,3,5-tri-O-acetyl-beta-L-fucofuranoside. Fusion of the furanose tetraacetates with phosphoric acid gave a mixture of the fucofuranosyl phosphates in which the beta-anomer predominated (beta/alpha= 2.4). Anomeric pairs in the fucofuranose series appear to be distinguishable by the chemical shift of the C-6 methyl protons, as already shown by Sinclair and Sleeter in the pyranose series.
D005643:Fucose; D006027:Glycosides; D006600:Hexosephosphates / Q000138:chemical synthesis*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D008968:Molecular Conformation
D006027:Glycosides; D006600:Hexosephosphates; D005643:Fucose