Analysis of the reactivity of the dithioacetal mono-S-oxide 1-deoxy-1-ethylsulfinyl-1-ethylthio-3,4-O-isopropylidene-D-erythritol under different conditions of reduction

The chemistry of dithioacetal mono-S-oxides has not been studied very frequently. Their usual chemistry aims at recovering the carbonyl function by a sequence of reduction and hydrolysis. The results of the transformation of the dithioacetal mono-S-oxides of 1-deoxy-1-ethylsulfinyl-1-ethylthio-3,4-O-isopropylidene-D-erythritol, 2, under different reduction conditions, are reported in this paper. We also report how the coexistence of functoinal groups influences the resulting products. Hence, reductions with LiAlH4, Ph3P, (Me2N)3P, (CF3CO)2O–NaI and AcONa-Ac2O under Pummerer-type rearrangements have been studied.