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

Abstract

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.