Acid-mediated N-iodosuccinimide-based thioglycoside activation for the automated solution-phase synthesis of α-1,2-linked-rhamnopyranosides

Pure and Applied Chemistry Journal

Carbohydrate structures are often complex. Unfortunately, synthesis of the range of sugar combinations precludes the use of a single coupling protocol or set of reagents. Adapting known, reliable bench-chemistry reactions to work via automation will help forward the goal of synthesizing a broad range of glycans. Herein, the preparation of di- and tri-saccharides of alpha 1→2 rhamnan fragments is demonstrated using thioglycoside donors with the development for a solution-phase-based automation platform of commonly used activation conditions using N-iodosuccinimide (NIS) with trimethylsilyl triflate. Byproducts of the glycosylation reaction are shown to be compatible with hydrazine-based deprotection conditions, lending broader functionality to this method as only one fluorous-solid-phase extraction step per coupling/deprotection cycle is required.

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Acid-mediated N-iodosuccinimide-based thioglycoside activation for the automated solution-phase synthesis of α-1,2-linked-rhamnopyranosides

Victoria R. Kohout ^a, Alyssa L. Pirinellia ^a and Nicola L. B. Pohl b ^a

^a University of Minnesota Morris, 600 E. 4thSt., Morris, MN 56267, USA

^b Indiana University Bloomington, 800 E. Kirkwood Ave, Bloomington, IN 47408, USA

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Pure and Applied Chemistry

https://doi.org/10.1515/pac-2019-0307

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