Synthesis of L-fucose 2-, 3-, and 4-sulphates.
Treatment of L-fucose with an excess pf pyridine-sulphur trioxide gave an equilibrium mixture of mono-, di-, and tri-sulphates. L-Fucose was sulphated under optimal conditions for monosulphate formation, and the monoester fraction was isolated by chromatography on DEAE-cellulose. The isomeric L-fucose 2-, 3-, and 4-sulphates (1-3) were separated on a DEAE-cellulose column by elution with borate buffer. The structures of 1-3 were established by electrophoresis, colour tests, periodate oxidation, and, for the 2-isomer, by comparison with a specimen of 1 that had been definitively synthesised via methyl 3,4-O-isopropylidene-alpha-L-fucopyranoside (6) and methyl alpha-L-fucopyranoside 2-(barium sulphate) (5). The latter was rapidly hydrolysed in hot, dilute acetic acid to 1 and methyl alpha-L-fucopyranoside (4).
D055598:Chemical Phenomena; D002621:Chemistry; D005643:Fucose; D007536:Isomerism; D008722:Methods; D009904:Optical Rotation; D010084:Oxidation-Reduction; D013463:Sulfuric Acid Esters / Q000138:chemical synthesis*; D013464:Sulfuric Acids / Q000138:chemical synthesis*
D013463:Sulfuric Acid Esters; D013464:Sulfuric Acids; D005643:Fucose