Article
Extending the S-benzimidazolyl (SBiz) platform: N-alkylated SBiz glycosyl donors with the universal activation profile
Pure Applied Chemistry
(2017)
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
Disciplines
Publication Date
September, 2017
DOI
10.1515/pac-2017-0112
Publisher Statement
10.1515/pac-2017-0112
Citation Information
Scott J. Hasty, Nigam Rath and Alexei V. Demchenko. "Extending the S-benzimidazolyl (SBiz) platform: N-alkylated SBiz glycosyl donors with the universal activation profile" Pure Applied Chemistry Vol. 89 Iss. 9 (2017) p. 1321 - 1331 Available at: http://works.bepress.com/nigam-rath/381/
Creative Commons license
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