Large-scale synthesis of beta-L-fucopyranosyl phosphate and the preparation of GDP-beta-L-fucose.

A practical 15-mmol large-scale synthesis of beta-L-fucopyranosyl dicyclohexylammonium phosphate from L-fucose in 63% overall yield was developed. The synthesis took advantage of a neighboring Bz-2 group participating in a Koenigs-Knorr-like glycosylation. The sugar phosphate was transformed into the activated sugar nucleoside, guanosine diphosphate beta-L-fucopyranose, on a gram scale.