Synthesis of alpha,alpha-, alpha,Beta-, and Beta,Beta-(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 alpha,alpha, alpha,beta, and beta,beta 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 alpha,alpha-(dimaltoside)s and cinnamyl alcohol are briefly discussed.
Tsuzuki
M
M
Institute of Bioorganic Chemistry, Nakahara-ku Kawasaki 211, Japan.
Tsuchiya
T
T
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D008958:Models, Molecular; D008969:Molecular Sequence Data; D020005:Propanols / Q000737:chemistry*; D013402:Sugar Alcohols / Q000138:chemical synthesis*
D020005:Propanols; D013402:Sugar Alcohols; C020722:cinnamyl alcohol