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Issue 0, 1980
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Alkyloxytris(dimethylamino)phosphonium salts. Part 21. Anomeric hydroxy-group activation of 2,3:4,6-di-O-isopropylidene-α-D-mannopyranose, thioglycosylation and glycosylation

Abstract

The action of carbon tetrachloride and tris(dimethylamino)phosphine at low temperature on 2,3:4,6-di-O-isopropylidene-α-D-mannopyranose affords the α anomeric form of the corresponding alkoxytris(dimethylamino)phosphonium chloride. The condensation of aromatic thiols with this salt leads to β-thiomannosides by an SN2 process and the condensation of alcohols, preceded by the action of silver salts in order to avoid the formation of the glycosyl chlorides, yields a mixture of α- and β-mannosides.

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Article type: Paper
DOI: 10.1039/P19800000381
Citation: J. Chem. Soc., Perkin Trans. 1, 1980,0, 381-384

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    Alkyloxytris(dimethylamino)phosphonium salts. Part 21. Anomeric hydroxy-group activation of 2,3:4,6-di-O-isopropylidene-α-D-mannopyranose, thioglycosylation and glycosylation

    F. Chretien, Y. Chapleur, B. Castro and B. Gross, J. Chem. Soc., Perkin Trans. 1, 1980, 0, 381
    DOI: 10.1039/P19800000381

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