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Issue 8, 1994
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Glycosides. Part 1. New synthesis of 1,2-trans O-aryl glycosides, via tributyltin phenoxides

Abstract

A new method of glycosidation of phenols has been studied. The reaction of tributyltin phenoxides 2 with 1,2,3,4,6-penta-O-acetyl-D-hexopyranosides 3, 7 and 9, in the presence of tin tetrachloride is described. Glycosides 4, 8 and 10 have been isolated in good yields with high 1,2-trans selectivity. The tributyltin phenoxides 2 have been isolated in quantitative yields, starting from phenols 1 and Bu3SnOMe. This simple method starts from the stable peracetylated sugar, an intermediate of easy access.

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Article type: Paper
DOI: 10.1039/P19940000985
Citation: J. Chem. Soc., Perkin Trans. 1, 1994,0, 985-988

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    Glycosides. Part 1. New synthesis of 1,2-trans O-aryl glycosides, via tributyltin phenoxides

    F. Clerici, M. L. Gelmi and S. Mottadelli, J. Chem. Soc., Perkin Trans. 1, 1994, 0, 985
    DOI: 10.1039/P19940000985

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