Synthèse des l-fucose et l-(3-2H)fucose à partir du d-mannose

摘要: Abstract Oxidation with the dimethyl sulfoxide-acetic anhydride reagent of methyl 2- O -acetyl-4,6- -benzylidene-α- d -mannopyranoside, obtained in quantitative yield from corresponding 4,6-benzylidene acetal by stereoselective opening a 2,3-orthoester, led good to - arabino -hexopyranosid-3-ulose, which was reduced either sodium borohydride or borodeuteride into 4,6- -altropyranoside its 3- 2 H derivative. A sequence involving C-6 halogenation-dehydrohalogenation followed catalytic hydrogenation resulting 6-deoxy-α- -hex-5-enopyranoside gave 6-deoxy-β- l -galactopyranoside (methyl β- -fucopyranoside) and then α- -fucose, an overall 24% respect starting -mannopyranoside.