The remote effect of vicinal large groups on the anomeric equilibrium: 2-methoxy-cis- and -trans-5,6-dimethyltetrahydropyrans |
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| Authors: | D T Sepp and C B Anderson |
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| Institution: | Department of Chemistry, University of California, Santa Barbara, California 93106 U.S.A. |
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| Abstract: | The anomeric equilibrium of 2-methoxy-trans-5,6-dimethyltetrahydropyran was found to have an enhanced fraction of axial methoxyl compared to 2-methoxy-4- or 6-methyltetrahydropyran. The 2-methoxy-cis-5,6-dimethyltetrahydropyran did not. The enhanced anomeric effect is attributed to a steric repulsion between the trans vicinal Me groups. A similar effect is postulated for methyl glucoside and glucose pentaacetate. |
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