Di-O-isopropylidene derivatives of D-glucose and D-mannose were synthesized, and characterized based on different spectral techniques. Both the derivatives exhibit different extents of intra and inter molecular hydrogen bonding in different solvents. Absorption, FT-IR and NMR studies in different solvents shows 2,3:5,6-di-O-isopropylidene-D-mannofuranose derivative to exhibit hydrogen bonding different from the corresponding D-glucofuranose derivative.