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S-Adamantyl Group Directed Site-Selective Acylation: Applications in Streamlined Assembly of Oligosaccharides.


ABSTRACT: 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 ??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.

SUBMITTER: Blaszczyk SA 

PROVIDER: S-EPMC6663581 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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S-Adamantyl Group Directed Site-Selective Acylation: Applications in Streamlined Assembly of Oligosaccharides.

Blaszczyk Stephanie A SA   Xiao Guozhi G   Wen Peng P   Hao Hua H   Wu Jessica J   Wang Bo B   Carattino Francisco F   Li Ziyuan Z   Glazier Daniel A DA   McCarty Bethany J BJ   Liu Peng P   Tang Weiping W  

Angewandte Chemie (International ed. in English) 20190530 28


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 π 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 activat  ...[more]

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