Synthesis of 6-Deoxy-4-O-methyl-6-phenylphosphinyl-D-fructopyranoses. The First P-in-the-Ring Analogs of a Ketose

Article abstract of DOI:10.1246/cl.1991.1439

Treatment of D-fructose with 2-methoxypropene-TsOH, followed by tosylation, gave 1,3-O-isopropylidene-6-O-tosyl-α-D-fructofuranose (5).Methyl 6-deoxy-6-<(ethoxy)phenylphosphinyl>-4-O-methyl-α-D-fructofuranoside (8) was derived from 5 in a 3 step sequence (67percent overall yield).Compound 8 was converted into the title compounds, which were characterized as the 1,3,5-tri-O- and 1,2,3,5-tetra-O-acetyl derivatives.