Synthesis and Supramolecular Chemistry of Carbohydrate Derivatives and Development of Methodologies

Mukherjee, Somnath (2012) Synthesis and Supramolecular Chemistry of Carbohydrate Derivatives and Development of Methodologies. PhD thesis, Indian Institute of Science Education Research Kolkata.

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Abstract

The thesis first illustrates a general introduction on the biological significance of carbohydrates, its use as therapeutics, different techniques of glycosidic bond formation and then it describes the supramolecular chemistry of low molecular weight carbohydrate derivatives such as sugar-derived gels, liquid crystals and single crystals and their potential applications in various fields. Then it takes up the up-to-date review on sugar-derived low molecular weight organic gelators describing gelation phenomena, gel characterization and their applications in various fields. The last portion of this chapter highlights the correlation study between crystal structures and gelling/non gelling behaviour. After that it deals with a simple eco-friendly carbohydrate organogelator for phase selective gelation of oils from oil-water mixtures at room temperature, dye removal for water purification and X-ray crystal structure in the monohydrate form. Later, it represents five simple, biodegradable and easily synthesizable low molecular weight galactose derivatives. Among these galactoside 1 serves as a thermo reversible LMOG. Single crystal X-ray structures of these five galactose derivatives has also been reported and studied. This chapter also deals with the mechanical properties study of these crystals and interestingly, the bending phenomena was observed in the single crystal of one of the galactosides. Last portion of this chapter deals with the correlation study between single crystal structures (Hydrogen bonding network) of these five galactosides and their gelling/ non gelling behaviour. Then, it goes on to demonstrate the use of La(OTf)3 as an efficient promoter system for ıhioglycoside activation in conjunction with N-iodosuccinimide. Moving forward, it deals with the use of Cellulose sulphuric acid as an efficient, biodegradable and recyclable solid acid catalyst for the hydrolysis of thioglycosides in conjugation with Niodosuccinimide. At the end, it describes the syntheses of a trisaccharide related to the related to the exocellular polysaccharide from Rhodococcus SP. RHA1

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