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Issue 17, 1993
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Glycosylation of phenols: preparation of 1,2-cis and 1,2-trans glycosylated tyrosine derivatives to be used in solid-phase glycopeptide synthesis

Abstract

The synthesis of four building blocks, Nα-Fmoc-Tyr(Ac4-β-D-Glc)-OPfp 6, Nα- Fmoc-Tyr(Bz4-α-D-Glc)-OPfp 16, Nα-Fmoc-Tyr[Ac3-α-D-Glc]-(1→4)-Ac3-[β-D-Glc]-OPfp 9 and Nα-Fmoc-Tyr[Bz4-α-D-Glc-(1 →4)-Bz3-α-D-Glc]-OPfp 19, suitable for solid-phase glycopeptide synthesis is described. Several different glycosylation procedures were evaluated for this purpose. A remarkable solvent effect on the α:β ratio was observed on going from dichloromethane to the nucleophilic solvent acetonitrile for the glycosylation reactions promoted by silver triflate with participating protecting groups in the 2-position of the glycosyl donor.

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Article type: Paper
DOI: 10.1039/P19930002119
Citation: J. Chem. Soc., Perkin Trans. 1, 1993,0, 2119-2129

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    Glycosylation of phenols: preparation of 1,2-cis and 1,2-trans glycosylated tyrosine derivatives to be used in solid-phase glycopeptide synthesis

    K. J. Jensen, M. Meldal and K. Bock, J. Chem. Soc., Perkin Trans. 1, 1993, 0, 2119
    DOI: 10.1039/P19930002119

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