Recent years have witnessed a great deal of interest in the design and synthesis of small molecules, which can mimic complex carbohydrates of vital importance in various life processes. Carbasugars constitute one such class of molecules among several others, in which ring oxygen of sugar is replaced by a methylene unit. Several approaches have been reported in the literature for the synthesis of carbasugars emanating both from carbohydrate and non-carbohydrate sources. While the carbohydrate-based approaches require extensive prote'ction-deprotection maneuver, the non-carbohydrate-based approaches generally have problems of diastereoselection and introduction of chirality.
In the context of synthesis of carbasugars, we envisaged that a suitable derivative of i bicyclo[2.2.1]heptane (norbornyl system), could serve as a carbasugar equivalent provided the
inherent cyclohexane ring could be disengaged through a tactical cleavage of C1-C7 or C4-C7 bonds. In the present thesis entitled "Synthesis of carbasugars and other structurally related
motifs", we have established the carbasugar-norbornyl system equivalence by using 7-* oxobicyclo[2.2.1]hept~5-en-2~yl acetate as precursor . While the tactical cleavage of C1-C7 bond was employed in the synthesis of carbasugars, the C4-G7 bond cleavage provided access to a new class of carbasugars i.e. "confused" carbasugars* The quest for stronger and specific inhibitors of glycosidases led us to synthesize a diverse array of polyoxygenated compounds in this new family of carbasugars.
The thesis has been organized under five main sections: I. Introduction, II. Results & Discussion, III. Experimental, IV. Spectra, and V. References where we have narrated our I synthetic efforts with suitable literature citations.
| Identifer | oai:union.ndltd.org:IISc/oai:etd.ncsi.iisc.ernet.in:2005/247 |
| Date | 05 1900 |
| Creators | Talukdar, Pinaki |
| Contributors | Mehta, Goverdhan |
| Publisher | Indian Institute of Science |
| Source Sets | India Institute of Science |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis and Dissertation |
| Format | 2074194 bytes, application/pdf |
| Rights | I grant Indian Institute of Science the right to archive and to make available my thesis or dissertation in whole or in part in all forms of media, now hereafter known. I retain all proprietary rights, such as patent rights. I also retain the right to use in future works (such as articles or books) all or part of this thesis or dissertation. |
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