Effect of 2- O-Benzoyl para-Substituents on Glycosylation Rates

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From a series of competition experiments, we have explored the degree to which various para-substituents (CN, Br, H, OMe, pyrrolidino) of a 2-O-benzoyl functionalized glucosyl donor of the thioglycoside type affect the rate of glycosylation under N-iodosuccinimide/triflic acid activation. As expected, electron-withdrawing groups were found to decrease the rate of glycosylation, whereas electron-donating groups resulted in the opposite outcome, underscoring the influence on the reaction rate exerted by a participating group. On this basis, a Hammett linear free-energy relationship was established (R2 = 0.979, P = 0.6), offering fundamental insight into the magnitude of anchimeric assistance in glycosylation chemistry.

OriginalsprogEngelsk
TidsskriftACS Omega
Vol/bind3
Nummer6
Sider (fra-til)7117-7123
Antal sider7
ISSN2470-1343
DOI
StatusUdgivet - 30 jun. 2018

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