Interglycosidic Acetals IV. Preparation and Regioselective Cleavage of Phenyl 2,2': 4,6: 4',6'-Tri-O-benzylidene-1-thio-.BETA.-laminaribiosides.

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  • Sakairi Nobuo
    Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University
  • Okazaki Yasunori
    Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University
  • Furukawa Jun-ichi
    Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University
  • Kuzuhara Hiroyoshi
    Department of Engineering, Saitama University
  • Nishi Norio
    Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University
  • Tokura Seiichi
    Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University

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  • Interglycosidic Acetals IV. Preparation and Regioselective Cleavage of Phenyl 2,2′ : 4,6 : 4′,6′-Tri-<i>O</i>-benzylidene-1-thio-<i>β</i>-laminaribiosides

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A (+)-10-Camphorsulfonic acid-catalysed acetal exchange reaction of phenyl 1-thio-β-laminaribioside using 3.5 molar equivalents of α,α-dimethoxytoluene gave a tris(benzylidene acetal), which was isolated and characterized as phenyl 3′-O-acetyl-2,2′ : 4,6 : 4′,6′-tri-O-benzylidene-1-thio-β-laminaribioside, and the corresponding 3′-O-benzyl derivative 6. Upon a treatment with pyridinium p-toluenesulfonate, the interglycosidic 2,2′-acetal in 6 underwent selective cleavage to give the 2,2′-diol. Additionally, a reductive ring-opening reaction of 6 with lithium aluminium hydride/anhydrous aluminium chloride, followed by O-acetylation, gave the 2,6,6′-O-acetyl-4,2′,3′,4′-tetra-O-benzyl derivative in 73% yield. A different regioselectivity was observed in the reduction of 6 with borane-trimethylamine adduct/anhydrous aluminium chloride or sodium cyanotrihydroborate/methanesulfonic acid, giving the corresponding 2,4,4′-triol as the major product.

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