Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 11, Pages 2457-2462Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500001
Keywords
Synthetic methods; Biological activity; Carbohydrates; Glycosides; Glycal
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Funding
- Farmingdale State College-SUNY (CSTEP program)
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We herein report the synthesis of 2-deoxy-2-iodo-glycosylamides, glycosylurea, N-glycosylbenzotriazole, and N-glycosyl imidazole by addition reaction of trimethylsilyl amides, imidazoles, and benzotriazoles to D-glucal in the presence of N-iodosuccinimide and propionitrile at 0 degrees C. Two diastereomers were isolated ? the -mannose and -gluco isomers. Reduction and substitution reaction of the iodine at position C-2 led to formation of various 2-deoxy-N-glycosides and 2-hydroxy--D-glucopyranosylamide. The newly generated compounds were screened for their inhibitory activity against various enzymes that included Nav1.7 sodium ion voltage-gated channel in HEK293 cells and the results are discussed.
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