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A novel series of chiral liquid crystalline tripedes Glucoside and Mannoside derivatives G(n) and M(n) (n=1-3) have been synthesised. The inner cores consist of methyl α-D-Glucoside G or methyl α-D-Mannoside M, regioselectively functionalised at the less hindered position C6, with tert-butyldimethylsilyl (TBDMS), hydroxyl or carboxylic acid moieties. The cores, which can acquire several flexible conformations, are attached to rod-like smectogenic-preferring cyanobiphenyl units, by means of a flexible hexanoyl spacer. These Glyco-Supermolecules exhibit chiral nematic (N*) and smectic A (SmA) phases. The combined effects of core chirality and functional groups on thermal and mesomorphic characteristics are discussed.