Development of new synthetic strategies for aminocyclitols

Demir (Davulcu), Emine
Cyclitols are of great importance due to their biological activities playing a crucial role in living organisms as well as their synthetic usefulness in the synthesis of other natural compounds or pharmaceuticals. In this study, new synthetic strategies leading to the aminocyclitols were investigated. The synthesis of aminoconduritol and aminoinositol derivatives (173 and 174) were achieved starting from easily available compound, 7-oxa-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (166) obtained from the Diels-Alder reaction of furan and maleic anhydride. The anhydride functionality in 166 was converted into the half-ester 169 by desymmetrization in methanol. The carboxylic acid moiety in the molecule was used to obtain urethane functionality by making use of Curtius rearrangement. After the cleavage of oxa-bridge with the help of a Lewis acid the aminoconduritol derivative 173 was synthesized. The cis-dihydroxylation of 173 with osmium tetroxide resulted in the formation of inositol derivative 174. Consequently, we developed a new methodology for the synthesis of aminocyclitol derivatives.


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Kaya, Nihal; Balcı, Metin; Department of Chemistry (2009)
Cyclitols have attracted a great deal of attention in recent years because of diverse biological activities exhibited by them and also synthetic usefulness in the synthesis of other natural compounds or pharmaceuticals. The presence of hydroxymethyl groups in many cyclitols units building natural products is also attracting a remarkable attention. In this study, novel synthetic strategies leading to cyclitol derivatives including hydroxymethyl groups were investigated and the syntheses of bis-homoinositol d...
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Synthesis of five-membered heteroaromatic compounds such as pyrazoles, isoxazoles and 1,2,4-oxadiazoles are important for pharmaceutical industry and material science due to their applications. Although there are many methods to prepare such compounds, new variants continue to appear since they exhibit a wide range of biological and medicinal activities. In this thesis, new methods were developed for the synthesis of 4-iodopyrazoles, pyrazoles, isoxazoles, 1,2,4-oxadiazoles and/or 1,2,4-oxadiazepines. In th...
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A general synthetic strategy is developed to synthesize water soluble receptors by employing tripodal system based on a cyclotriphosphaze platform. The developed model is successfully synthesized and characterized by using elemental analysis, FT-IR, MALDI-TOF, H-1 NMR, C-13 NMR and P-31 NMR techniques. The fluorescence sensing performance of prepared water soluble tripodal systems were evaluated by UV/Vis and fluorescence spectroscopies. According to obtained results, two novel water-soluble sensing platfor...
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Chitosan is a natural polysaccharide which finds use in various biomedical applications due to its important biological properties. Layer-by-layer (LbL) technique is a practical and economical method to functionalize surfaces using interacting polymer pairs. LbL technique can also be used to construct polymer platforms for controlled release of functional molecules from a surface. In this thesis, ultra-thin polymer coatings were prepared using Chitosan and two different weak polyacids, i.e. Tannic Acid (TA)...
Citation Formats
E. Demir (Davulcu), “Development of new synthetic strategies for aminocyclitols,” M.S. - Master of Science, Middle East Technical University, 2003.