SYNTHESE DES L-FUCOSE ET L-(3-(2)H)FUCOSE A PARTIR DU D-MANNOSE

Article abstract of DOI:10.1016/S0008-6215(00)80712-0

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