SYNTHESIS OF 3-DEOXY-3-FLUORO-D-MANNOSE AND 4-DEOXY-4-FLUORO-D-MANNOSE

Article abstract of DOI:10.1016/S0008-6215(00)90949-2

Addition of potassium cyanide to 2-deoxy-2-fluoro-D-arabinose (1) at pH 7.8 followed by catalytic hydrogenation over palladium-barium sulfate (5percent) produced 3-deoxy-3-fluoro-D-glucose (4) and 3-deoxy-3-fluoro-D-mannose (5) in 25 and 40 percent isolated yields, respectively.The epimeric sugars were purified by passage through a column of Dowex-50W x 8 (Ca²⁺).In a similar manner, 3-deoxy-3-fluoro-D-arabinose (6) was converted into 4-deoxy-4-fluoro-D-glucose (9) and 4-deoxy-4-fluoro-D-mannose (10) in 27 and 45 percent isolated yields, respectively.Deoxyfluorohexoses 4,5,9 and 10 enriched with carbon-13 and crbon-14 at C-1 have been prepared by this procedure.