Synthesis of α,α-, α,β-, and β,β-(dimaltoside)s of ethane-1,2-diol, propane-1,3-diol, and butane-1,4-diol: A proposal for an initial adhesion mode

Nine dimaltoside derivatives of ethane-1,2-diol, propane-1,3-diol, and butane-1,4-diol having the α,α, α,β, and β,β anomeric configurations at the linkage sites have been synthesized. Suitably protected maltosyl halides or a 1-(phenylthio) derivative were condensed with the foregoing diols and the resulting monomaltosyl derivatives were further condensed with the maltosyl donors to give, after deprotection, the title compounds. Their structures were fully characterized by NMR spectroscopy. Interactions between the three α,α-(dimaltoside)s and cinnamyl alcohol are briefly discussed.