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Issue 22, 1994
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Synthesis of glycosyltyrosine building blocks for solid-phase glycopeptide assembly: use of aryl tert-butyl ethers as glycosyl acceptors in aromatic glycosylations

Abstract

The synthesis of the suitably protected building blocks for solid-phase glycopeptide synthesis, Nα-Fmoc-Tyr(Bz4-β-D-Gal)-OPfp 3, Nα-Fmoc-Tyr(Bz4-α-D-Gal)-OPfp 4, Nα-Fmoc-Tyr(Bz3-α-L-Rha)-OPfp 6, N-α-Fmoc-Tyr[Bz3-α-L-Rha(1→3)-Bz3-β-D-Gal]-OPfp 18, and Nα-Fmoc-Tyr[Bz4-α-D-Glc(1→4)-Bz3-α-D-Glc(1→4)-Bz3-β-D-Glc]-OPfp 20, are described. The synthesis involves the coupling of the corresponding glycosyl bromides with the aryl tert-butyl ether Nα- Fmoc-Tyr(But)-OPfp 1, using silver trifluoromethanesulfonate as promoter.

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Article type: Paper
DOI: 10.1039/P19940003287
Citation: J. Chem. Soc., Perkin Trans. 1, 1994,0, 3287-3294

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    Synthesis of glycosyltyrosine building blocks for solid-phase glycopeptide assembly: use of aryl tert-butyl ethers as glycosyl acceptors in aromatic glycosylations

    A. Vargas-Berenguel, M. Meldal, H. Paulsen, K. J. Jensena and K. Bock, J. Chem. Soc., Perkin Trans. 1, 1994, 0, 3287
    DOI: 10.1039/P19940003287

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