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

Victoria R. Kohout; Alyssa L. Pirinelli; Nicola L.B. Pohl

doi:10.1515/pac-2019-0307

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

Victoria R. Kohout, Alyssa L. Pirinelli, Nicola L.B. Pohl

Chemistry (Morris)

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	1243-1255
Number of pages	13
Journal	Pure and Applied Chemistry
Volume	91
Issue number	7
DOIs	https://doi.org/10.1515/pac-2019-0307
State	Published - Jul 1 2019

Bibliographical note

Funding Information:
Acknowledgements: This work was supported in part by Indiana University and the National Institute of General Medical Sciences (Funder Id: http://dx.doi.org/10.13039/100000057, 5U01GM116248-02). We thank Dr. R. Saliba for his input and assistance with the automation platform and Prof. A. Flood and his research group for use of their Agilent 1200 Preparatory HPLC system.

Publisher Copyright:
© 2019 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/ 2019.

Keywords

ICS-29
automated synthesis
carbohydrates
synthesis

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10.1515/pac-2019-0307

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abstract = "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

Abstract

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