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Synthesis and Technology of Taxol C-13 Side Chain

Author: FanQiangZuo
Tutor: DuYang
School: Nanjing University of Technology and Engineering
Course: Chemical processes
Keywords: Taxol C-13 sidechain The chiral auxiliary Synthesis Process optimization
CLC: TQ463.4
Type: Master's thesis
Year: 2010
Downloads: 150
Quote: 0
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Abstract


Taxol is extracted from the bark of Taxus brevifolia , is a two terpene compounds , it has a very good effect in many cancers such as ovarian cancer . The natural yew in the number of the world rarely , content is minimal, mainly through the C-13 side chain 10 - deacetyl baccatin III docking synthetic paclitaxel . Therefore, taxol C-13 sidechain of the synthesis and process has a great practical value . By the synthetic route of the C-13 sidechain , the comparison of the various methods , to determine the best synthetic methods . The method of chloroacetyl chloride with chiral menthol as a raw material, first synthesized chloroacetate , and then with benzaldehyde by to Darzen condensation synthesis ( 2R, 3R ) -2,3 - epoxy-3 - phenyl- propionate again by azide , restore , aminolysis , hydrolysis reaction synthesis of chiral paclitaxel C-13 side chain . While also optimizing the reaction process, avoiding column chromatography . This method raw materials are readily available and relatively mild reaction conditions , and low cost , and favor industrial production . Papers optimized synthetic routes, the analysis of a variety of conditions (time, temperature , feeding ratio, amount of catalyst , etc.) of the influence of the change on the reaction yield and purity , and to determine the optimum reaction conditions . Each step products undergo melting point determination , NMR , IR , mass spectrometry and other analytical tools to the characterization , analysis showed that the product obtained are in line with the target product , so you can confirm the feasibility of the design .

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