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Extending the S-benzimidazolyl (SBiz) platform: N-alkylated SBiz glycosyl donors with the universal activation profile
Pure and Applied Chemistry (2017)
  • Scott J. Hasty, University of Missouri–St. Louis
  • Nigam P. Rath, University of Missouri–St. Louis
  • Alexei V. Demchenko, University of Missouri–St. Louis
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.
Keywords
  • carbohydrates; glycosylation; ICS-28; oligosaccharides; synthesis
Publication Date
January 28, 2017
DOI
10.1515/pac-2017-0112
Citation Information
Scott J. Hasty, Nigam P. Rath and Alexei V. Demchenko. "Extending the S-benzimidazolyl (SBiz) platform: N-alkylated SBiz glycosyl donors with the universal activation profile" Pure and Applied Chemistry Vol. 89 Iss. 9 (2017) p. 1321 - 1331
Available at: http://works.bepress.com/alexei-demchenko/29/
Creative Commons license
Creative Commons License
This work is licensed under a Creative Commons CC_BY-NC-ND International License.