Practical Synthesis of Building Blocks for Oligosaccharides Containing the β-d-Galp-(1→3)-β-d-GlcpNAc Motif

Sameh E. Soliman; Pavol Kováč

doi:10.1055/s-0033-1340620

Synthesis, Table of Contents

Synthesis 2014; 46(06): 748-751
DOI: 10.1055/s-0033-1340620

practical synthetic procedures

Practical Synthesis of Building Blocks for Oligosaccharides Containing the β-d-Galp-(1→3)-β-d-GlcpNAc Motif

Authors

Sameh E. Soliman

^aDepartment of Chemistry, Faculty of Science, Alexandria University, Alexandria 21321, Egypt

^bNIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA Fax: +1(301)4805703 Email: kpn@helix.nih.gov
Pavol Kováč*

^bNIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA Fax: +1(301)4805703 Email: kpn@helix.nih.gov

Abstract

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Abstract

An efficient, new pathway for the synthesis of the title sequence has been developed. The sequence has been obtained as a glycosyl donor, β-d-Galp-(1→3)-β-d-GlcpNAc-1-SEt, or equipped with a linker (spacer) suitable for conjugation to other molecules, β-d-Galp-(1→3)-β-d-GlcpNAc-1-(OCH₂CH₂)₃N₃. Both disaccharides have been obtained in crystalline condition for the first time and fully characterized. The existing synthesis of the intermediate disaccharide glycosyl donor was improved by conducting the silver triflate mediated glycosylation under base-deficient conditions in the presence of 1,1,3,3-tetramethylurea and in the absence of molecular sieves.

Key words

carbohydrates - oligosaccharides - synthetic methods - thioglycosides - protecting groups

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References

References
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Supplementary Material

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