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  • Title: Interglycosidic acetals. Part 3. Synthesis and structure determination of cyclic monobenzylidene acetals of cyclodextrin derivatives bridging between two contiguous D-glucopyranosyl residues.
    Author: Sakairi N, Nishi N, Tokura S, Kuzuhara H.
    Journal: Carbohydr Res; 1996 Sep 23; 291():53-62. PubMed ID: 8864223.
    Abstract:
    Transacetalation of fully 6-O-pivaloylated alpha-, beta-, and gamma-cyclodextrins with benzaldehyde dimethylacetal in the presence of (+)-10-camphorsulfonic acid gave monobenzylidene acetals (4, 5, 6) in moderately good yields. Benzylation of the beta-cyclodextrin derivative 5 followed by acid-catalyzed hydrolysis of the benzylidene group and acetylation afforded a di-O-acetyl-non-adeca-O-benzyl derivative 9. NMR spectroscopic analysis of 9, including two-dimensional HOHAHA and 1H-(13)C correlation experiments revealed that the benzylidene group bridged the O-2 and O-3 positions of contiguous D-glucopyranosyl residues. Reductive ring-opening of the benzylidene acetal with lithium aluminum hydride/aluminum chloride afforded predominantly a 2(1)-O-unprotected derivative 10 in good yield.
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