The Anomeric EffectThe equilibrium preference of most glucosides for the alpha-anomer is referred to as the anomeric effect. If we take away the extraneous functions and substituents from the glucoside structure, it is reduced to the 2-substituted pyran shown on the left in the following diagram. As the two conformational equilibria in the diagram demonstrate, the anomeric effect for a methoxy substituent is sufficient to change the preference for equatorial orientation (a consequence of steric hindrance) to a preference for the axial orientation. The anomeric effect in this case has been estimated at over 1 kcal/mol, but it should be noted that hydrogen bonding in hydroxylic solvents influences this factor.
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