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.
Department of Chemistry, Harvard University, Cambridge, Massachusetts 02138.
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Adelhorst
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Whitesides
D002236:Carbohydrate Conformation; D005643:Fucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006154:Guanosine Diphosphate Fucose / Q000138:chemical synthesis* / Q000737:chemistry; D006600:Hexosephosphates / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy
D006600:Hexosephosphates; D007202:Indicators and Reagents; D006154:Guanosine Diphosphate Fucose; C081214:fucopyranosyl phosphate; D005643:Fucose