A dendronized carbohydrate thermotropic liquid crystal was synthesized by attaching wedge-shaped mesogens onto a carbohydrate core. These molecules self-organize into chiral columnar hexagonal mesophase with each column slice (4.5Å thicknesses) filled with average of two molecules. The supramolecular model was further optimized by molecular dynamics simulation. Moreover, chirality successfully expressed in columnar hexagonal mesophase by dendronized carbohydrate molecules may provide inspiration in searching for chiral mesophase of carbohydrate liquid crystals.