A Comparative Study of Glycosyl Thioimidates as Building Blocks for Chemical Glycosylation

Our results indicate that the reactivity and the activation profile of thioimidate glycosyl donors vary significantly depending on the endocyclic heteroatom (N,O,S). Reactivity diminishes in accordance with the following sequence: O > S > N; and this trend stands for a majority of promoters te...

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Bibliographic Details
Published in:Journal of carbohydrate chemistry 2013-07, Vol.32 (5-6), p.360-379
Main Authors: Ranade, Sneha C., Hasty, Scott J., Demchenko, Alexei V.
Format: Article
Language:English
Subjects:
Carbohydrates
Comparative studies
Glycosylation
Oligosaccharides
Thioimidates
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Summary:Our results indicate that the reactivity and the activation profile of thioimidate glycosyl donors vary significantly depending on the endocyclic heteroatom (N,O,S). Reactivity diminishes in accordance with the following sequence: O > S > N; and this trend stands for a majority of promoters tested. Acyclic glycosyl thioimidates were found to be generally less reactive than the respective cyclic counterparts. The difference in the reactivity was confirmed in direct competition experiments. These findings made possible a two-step one-pot selective activation using thioimidates as the anomeric leaving group of the glycosyl donor and temporary masking group of the glycosyl acceptor. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the supplemental file.
ISSN:0732-8303
1532-2327
DOI:10.1080/07328303.2013.826670