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The Staudinger/aza-Wittig/Grignard reaction as key step for the concise synthesis of 1-C-Alkyl-iminoalditol glycomimetics

TitleThe Staudinger/aza-Wittig/Grignard reaction as key step for the concise synthesis of 1-C-Alkyl-iminoalditol glycomimetics
Publication TypeJournal Article
Year of Publication2016
AuthorsZoidl, M, Santana, AGonzalez, Torvisco, A, Tysoe, C, Siriwardena, A, Withers, SG, Wrodnigg, TM
JournalCARBOHYDRATE RESEARCH
Volume429
Pagination62-70
Date PublishedJUN 24
ISSN0008-6215
Abstract

The scope of a one-pot tandem approach for the synthesis of C-1 alkyl iminoalditol derivatives with a Staudinger/aza-Wittig/Grignard cascade has been evaluated. The reaction conditions have been optimized for two azidodeoxy aldose substrates and a range of Grignard reagents. The nature of both, substrate as well as nucleophile, was found to control the stereoselectivity of the alkyl addition to the cyclic iminium intermediate at position C-1. This approach enabled the synthesis of a collection of C-alkyl iminoalditols, which were biologically evaluated as inhibitors against a set of standard glycoside hydrolases. All compounds were found to exhibit highly selective inhibition of beta-glucosidase activity. (C) 2016 Elsevier Ltd. All rights reserved.

DOI10.1016/j.carres.2016.04.006