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Issue 12, 1977
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Synthetic studies with carbonates. Part 11. D-Glucopyranose 1-carbonate derivatives; pyrolytic behaviour and use for glucosylation of phenols

Abstract

2,3,4,6-Tetra-O-acetyl-1-O-phenoxycarbonyl-β-D-glucopyranose (1), its 1-O-methoxycarbonyl analogue (3), and 2,3,4,6-tetra-O-benzoyl-1-O-phenoxycarbonyl-β-D-glucopyranose (5) underwent pyrolysis to give mixtures of various products whose composition depended on the structure of the starting material. However, the α-anomers of (1) and (3) were not susceptible to pyrolysis, even under more drastic conditions. Glucosylation reactions of phenols with the β-D-glucopyranose 1-carbonates were conducted autocatalytically to give the corresponding phenyl β-D-glucopyranoside derivatives in moderate yields. Especially useful was the synthesis of o-nitrophenyl and o-chlorophenyl glucopyranoside derivatives, which cannot be prepared through the Helferich's procedure, even under acid-catalysis conditions. A reaction mechanism involving an orthoester intermediate is suggested; such an intermediate was isolated and transformed into the corresponding glucopyranoside derivatives etc.

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Article type: Paper
DOI: 10.1039/P19770001382
Citation: J. Chem. Soc., Perkin Trans. 1, 1977,0, 1382-1390

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    Synthetic studies with carbonates. Part 11. D-Glucopyranose 1-carbonate derivatives; pyrolytic behaviour and use for glucosylation of phenols

    Y. Ishido, S. Inaba, A. Matsuno, T. Yoshino and H. Umezawa, J. Chem. Soc., Perkin Trans. 1, 1977, 0, 1382
    DOI: 10.1039/P19770001382

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