Dissection of the effects that govern thioglucoside and thiomannoside reactivity

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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.

OriginalsprogEngelsk
TidsskriftOrganic and Biomolecular Chemistry
Vol/bind16
Nummer13
Sider (fra-til)2277-2288
Antal sider12
ISSN1477-0520
DOI
StatusUdgivet - 1 jan. 2018

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