Chemistry
Stereoelectronic Effects in Anomeric Stabilization of Carbohydrates
Quick fact
The anomeric effect can be so strong that it overrides steric hindrance: in many sugars, the axial anomer is more abundant than the equatorial one, despite the 1,3-diaxial interactions.
Why this is interesting
You know that bulky groups in a ring usually prefer the roomier equatorial position—but in sugars, the opposite often happens. Why does an electronegative group like -OH sometimes prefer the more crowded axial spot?