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Issue 4, 1990
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Novel synthesis of aryl 2,3,4,6-tetra-O-acetyl-D-glucopyranosides

Abstract

The glycosidation of phenols with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl fluoride in the presence of BF3·OEt2 to give, predominantly, α-anomers has been studied. In the presence of an amine base, 1,1,3,3-tetramethylguanidine, however, enhanced β-selectivity was achieved. The former reaction provides a novel and useful synthesis of aryl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside whilst the latter is effective for the glycosidation of relatively hindered phenols.

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Article type: Paper
DOI: 10.1039/P19900001079
Citation: J. Chem. Soc., Perkin Trans. 1, 1990,0, 1079-1082

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    Novel synthesis of aryl 2,3,4,6-tetra-O-acetyl-D-glucopyranosides

    M. Yamaguchi, A. Horiguchi, A. Fukuda and T. Minami, J. Chem. Soc., Perkin Trans. 1, 1990, 0, 1079
    DOI: 10.1039/P19900001079

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