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. 2021 Apr 30;54(11):2552–2564. doi: 10.1021/acs.accounts.1c00021

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© 2021 The Authors. Published by American Chemical Society

Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).

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(a) Alternative S_N2 and S_N1 reaction pathways leading to formation of α- and β-glycosides from glycosyl triflate intermediates. CIP, SSIP, and SEIP stand for contact ion pair, solvent-separated ion pair, and solvent-equilibrated ion pair, respectively. (b) Calculated free energy differences between α- and β-glycosyl triflates for d-Man, d-Glc and d-All in the gas phase. (c) NMR detection of β-glycosyl triflate signals (red) in reaction mixtures from Glc (left) and All (right) donors. Estimated equilibrium constants for the anomerization process are given in green.