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Issue 13, 2018
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Dissection of the effects that govern thioglucoside and thiomannoside reactivity

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Abstract

Neighboring group effects were investigated in gluco- and manno-configured thioglycosides under NIS/TfOH activation. Donors possessing a 2-O-benzoyl group that are capable (1,2-trans) and incapable (1,2-cis) of exerting nucleophilic push were compared with donors possessing a participatory neutral 2-O-benzyl group. By using competition experiments between sets of glycosyl donors the direct effect of neighboring group participation and the electron withdrawing effect of the 2-O-benzoyl group could be separated. The study brings insight into how the stereochemistry of the 1 and 2 position and how the nature of the aglycon (Ph or Et) have a pronounced effect on glycosyl donor reactivity.

Graphical abstract: Dissection of the effects that govern thioglucoside and thiomannoside reactivity

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Publication details

The article was received on 01 Dec 2017, accepted on 15 Feb 2018 and first published on 15 Feb 2018


Article type: Paper
DOI: 10.1039/C7OB02968C
Citation: Org. Biomol. Chem., 2018,16, 2277-2288
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    Dissection of the effects that govern thioglucoside and thiomannoside reactivity

    M. Heuckendorff, L. T. Poulsen, C. Hedberg and H. H. Jensen, Org. Biomol. Chem., 2018, 16, 2277
    DOI: 10.1039/C7OB02968C

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