Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 28, Pages 9542-9546Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201903587
Keywords
acylation; carbohydrates; glycosylation; noncovalent interactions; synthetic methods
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Funding
- NIH [U01GM125290]
- NIH Chemistry-Biology Interface Training Grant [T32 GM008505]
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The site-selective functionalization of carbohydrates is an active area of research. Reported here is the surprising observation that the sterically encumbered adamantyl group directed site-selective acylation at the C2 position of S-glycosides through dispersion interactions between the adamantyl C-H bonds and the pi system of the cationic acylated catalyst, which may have broad implications in many other chemical reactions. Because of their stability, chemical orthogonality, and ease of activation for glycosylation, the site-selective acylation of S-glycosides streamlines oligosaccharide synthesis and will have wide applications in complex carbohydrate synthesis.
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