The molecular modeling program STR3DI32.EXE, and its molecular mechanics module, QVBMM, were used to simulate and evaluate the stereo-electronic effects in the pyranoid analogs of the derivatives of monosaccharides that are known to display the reverse anomeric effect. This study has confirmed the importance of bond dipoles, particularly hydrogen bonding, in these effects. This study also holds considerable implications for unraveling the chemistry of glycoside formation and hydrolysis.