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Synthesis And Application Of Diisopropylidene Of Monosaccharide

Posted on:2013-02-21Degree:MasterType:Thesis
Country:ChinaCandidate:D D HuFull Text:PDF
GTID:2211330371459880Subject:Applied Chemistry
Abstract/Summary:PDF Full Text Request
Protection hydroxyl of sugar ring by acetonide is widely used and diisopropylidene of monosaccharide has been applied widespread in carbohydrate chemistry. Topiramate, derived from diisopropylidene of D-fructose, is a novel anticonvulsant drug used for treatment of epileptic. Compared to other traditional anticonvulsant drugs, Topiramate has many advantages.In this thesis, the preparative methods of Topiramate were briefly reviewed, and then the synthesis route of Topiramate was designed. Topiramate was synthesized from D-fructose through condensation and sulfonylation, followed by ammonolysis with ammonium carbonate. Also according to the phenomenon and data, the reasonable mechanism of the reactions was presumed respectively, and factors which may affect the yield were found. The reactive conditions were optimized with a overall yield of 61%.Using D-fructose, D-glucose, D-galactose and D-mannose as starting material, several analogs of Topiramate with potential biological activity were synthesized in accordance with this method. Using some intermediates as starting material, several nitrate esters were prepared with potential biological activity in curing cardiovascular disease.
Keywords/Search Tags:Topiramate, analogue, anti-epileptic, nitrate ester, cardiovascular disease
PDF Full Text Request
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