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Synthesis of an H type 2 and a Y (Ley) glycoside from thioglycoside intermediates

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Abstract

The trisaccharide 2-(p-trifluoroacetamidophenyl)ethyl 2-acetamido-2-deoxy-4-O-[2-O-(α-l-fucopyranosyl)-β-d-galactopyranosyl]-β-d-glucopyranoside 1 and the tetrasaccharide 2-(p-trifluoroacetamidophenyl)ethyl 2-acetamido-2-deoxy-3-O-(α-l-fucopyranosyl)-4-O-[2-O-(α-l-fucopyranosyl)-β-d-galactopyranosyl]-β-d-glucopyranoside 2 were synthesized. Thioglycosides, suitably protected, activated directly with methyl trifluoromethanesulfonate or dimethyl(methylthio)sulfonium tetrafluoroborate or activated after bromine treatment with halophilic reagents, were used as glycosyl donors in the construction of the glycosidic linkages.

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Abbreviations

DMTSB:

dimethyl(methylthio)sulfonium tetrafluoroborate

Phth:

phthaloyl

MBn:

p-methoxybenzyl

ClBn:

p-chlorobenzyl

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Authors and Affiliations

  1. Organic Synthesis Department, BioCarb AB, S-223 70, Lund, Sweden

    Stinabritt Nilsson, Hans Lönn & Thomas Norberg

Authors
  1. Stinabritt Nilsson
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  2. Hans Lönn
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  3. Thomas Norberg
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Nilsson, S., Lönn, H. & Norberg, T. Synthesis of an H type 2 and a Y (Ley) glycoside from thioglycoside intermediates. Glycoconjugate J 6, 21–34 (1989). https://doi.org/10.1007/BF01047887

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  • DOI: https://doi.org/10.1007/BF01047887

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