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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen

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IMPACT FACTOR 2017: 5.294

CiteScore 2017: 3.42

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1365-3075
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Volume 89, Issue 9

Issues

Extending the S-benzimidazolyl (SBiz) platform: N-alkylated SBiz glycosyl donors with the universal activation profile

Scott J. Hasty
  • Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, St. Louis, MO 63121, USA
  • Other articles by this author:
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/ Nigam P. Rath
  • Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, St. Louis, MO 63121, USA
  • Other articles by this author:
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/ Alexei V. Demchenko
  • Corresponding author
  • Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, St. Louis, MO 63121, USA
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Published Online: 2017-04-28 | DOI: https://doi.org/10.1515/pac-2017-0112

Abstract

This article describes the development of alkylated S-benzimidazolyl (SBiz) imidates as versatile building blocks for chemical glycosylation. The SBiz imidates have been originally developed as a new platform for active-latent glycosylations and its utility was further extended to other common strategies for oligosaccharide synthesis. This article expands upon the utility of these compounds. We developed a general protocol for the synthesis of a series of N-alkylated SBiz glycosides from N-protected SBiz aglycones by Lewis acid-mediated coupling with glucose pentaacetate. The N-alkylated SBiz moiety was found to be stable under strong basic conditions which allowed us to obtain both armed and disarmed N-alkylated SBiz donors. These donors showed good reactivity at a variety of activation conditions, and generally provided high yields in glycosylations.

This article offers supplementary material which is provided at the end of the article.

Keywords: carbohydrates; glycosylation; ICS-28; oligosaccharides; synthesis

Article note:

A collection of invited papers based on presentations at the XXVIII International Carbohydrate Symposium (ICS-28), New Orleans, July 17–21, 2016.

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About the article

Published Online: 2017-04-28

Published in Print: 2017-08-28


Citation Information: Pure and Applied Chemistry, Volume 89, Issue 9, Pages 1321–1331, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2017-0112.

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