Document Type

Article

Publication Date

7-12-2019

Embargo Period

7-12-2020

Publication Title

Pure and Applied Chemistry

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.

Volume

91

Issue

7

First Page

1243

Last Page

1255

DOI

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

ISSN

1365-3075

Comments

This article also available through the publisher's website.

Rights

© 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

Primo Type

Article

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