Synthesis 2014; 46(06): 748-751
DOI: 10.1055/s-0033-1340620
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

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

Sameh E. Soliman
a  Department of Chemistry, Faculty of Science, Alexandria University, Alexandria 21321, Egypt
b  NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA   Fax: +1(301)4805703   Email: [email protected]
,
Pavol Kováč*
b  NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA   Fax: +1(301)4805703   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 29 November 2013

Accepted: 19 December 2013

Publication Date:
30 January 2014 (online)


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.

Supporting Information

 
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