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

Research output: Contribution to journalArticle

1 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 languageEnglish (US)
Pages (from-to)1243-1255
Number of pages13
JournalPure and Applied Chemistry
Volume91
Issue number7
DOIs
StatePublished - Jul 1 2019
Externally publishedYes

Keywords

  • ICS-29
  • automated synthesis
  • carbohydrates
  • synthesis

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