Iodophosphoryloxylation of carbon-carbon multibonds and its application toglycals

Iodophosphoryloxylation of carbon-carbon multibonds was attempted. Alkynes and cyclohexene were converted to the corresponding 1,2-iodophosphoryloxyla ted compounds in moderate to good yields with a trivalent iodine compound/i odine system, while glucal gave mainly the corresponding iodohydrin compoun d in this system. However, 2-deoxy-2-iodoglycosyl diphenylphosphinates were obtained from the corresponding glycals with a diphenylphosphinic acid/iod ine/potassium carbonate system in good yields. Moreover, triethylborane smo othly reduced 2-deoxy-2-iodoglycosyl diphenylphosphinates to 2-deoxyglycosy l diphenylphosphinates in a 1,4-cyclohexadiene solvent.