Langenhan, Joseph M. McLaughlin, Ryan P. Loskot, Steven A. Rozal, Leonardo M. S. Clay, Mackenzie Alaimo, Peter J. Using density functional theory to calculate the anomeric effect in hydroxylamine and hydrazide derivatives of tetrahydropyran <p>Little is known about the magnitude of the anomeric effect in N-glycosylated oxyamines and hydrazides, limiting efforts toward the design of chemoselective acceptors that impose a stereochemical preference on glycosylation reactions. Thus, density functional theory (DFT) calculations were conducted to estimate the magnitude of the anomeric effect in <i>N,O</i>-dimethyl-<i>N</i>-(tetrahydro-<i>2H</i>-pyran-2-yl)hydroxylamine (<b>1</b>) and <i>N'</i>-(tetrahydro-<i>2H</i>-pyran-2-yl)acetohydrazide (<b>3</b>). The results show that <i>N,O</i>-dimethyl-<i>N</i>-(tetrahydro-<i>2H</i>-pyran-2-yl)hydroxylamine (<b>1</b>) displays a significant anomeric effect (AE<sub>corr</sub> = 1.38 kcal/mol) and that <i>N'</i>-(tetrahydro-<i>2H</i>-pyran-2-yl)acetohydrazide (<b>3</b>) displays a modest anomeric effect (AE<sub>corr</sub> = 0.54 kcal/mol).</p> Anomeric effect;chemoselective glycosylation;conformational analysis;DFT calculations 2016-03-02
    https://tandf.figshare.com/articles/journal_contribution/Using_density_functional_theory_to_calculate_the_anomeric_effect_in_hydroxylamine_and_hydrazide_derivatives_of_tetrahydropyran/3081979
10.6084/m9.figshare.3081979