J. M. Langenhan, R. Mclaughlin, Steven A. Loskot
Feb 12, 2016
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Journal
Journal of Carbohydrate Chemistry
Abstract
ABSTRACT 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 N,O-dimethyl-N-(tetrahydro-2H-pyran-2-yl)hydroxylamine (1) and N'-(tetrahydro-2H-pyran-2-yl)acetohydrazide (3). The results show that N,O-dimethyl-N-(tetrahydro-2H-pyran-2-yl)hydroxylamine (1) displays a significant anomeric effect (AEcorr = 1.38 kcal/mol) and that N'-(tetrahydro-2H-pyran-2-yl)acetohydrazide (3) displays a modest anomeric effect (AEcorr = 0.54 kcal/mol). GRAPHICAL ABSTRACT