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Focusing on green chemistry protocols, a series of carbohydrate derivatives (5a–l) have been synthesized by Fischer glycosylation of α-D-glucose, D-xylose, and α-maltose with several nonpolar phenolic ester aglycones (3a–d) derived from menthol by employing solid-supported Si-H+ as the catalyst. In order to study the extent of mesomorphism in target molecules, the thermotropic behaviour has been studied by using the thermoanalytic DSC/TGA technique and polarized optical microscope. Phase transitions in the DSC thermograms of 5a–l with two endothermic melting point peaks and various exothermic crystalline transitions exhibits the existence of mesophases. However, optical photomicrographs revealed that the new glycopyranosides formed smectic A phases. Moreover, all the compounds (3a–d and 5a–l) were confirmed by FTIR and 1H NMR.