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Studies on the Synthesis of (-)-EGCG and SFN, X-Ray and Gram Scale Synthesis of 3,6-DCC

Author: DingTongJian
Tutor: CaoXiaoPing
School: Lanzhou University
Course: Organic Chemistry
Keywords: Alcohol compounds Natural Products Single crystal structure Master's degree thesis First reported Synthetic strategy Chiral center Intermolecular Asymmetric Synthesis Intramolecular
CLC: O629
Type: Master's thesis
Year: 2007
Downloads: 73
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Abstract


In this thesis, the natural product (-)-Epigallocatechin-3-gallate [(-)-EGCG] Synthesis and Sulforaphane (SFN) , and reported in the literature on the basis of 3,6-DCC gram synthesis optimization , and the first report of the single crystal structure of the compound and its precursor , the thesis is divided into four chapters : First , the recent progress in the Mitsunobu reaction , do a brief overview of the reaction mechanism , the highlight application of reaction in organic synthesis . Chapter 2 mainly studied the natural product ( - ) -EGCG the asymmetric synthesis of the green and SFN simple synthesis . In the process of synthesis of (-)-EGCG , abandoned shortcomings , lessons advantages . Sharpless asymmetric dihydroxylation before the preparation of the reaction body, to build a chiral center , and then Mitsunobu reaction through intramolecular and intermolecular bonding and at the same time to achieve completion of the configuration transformation of the skeleton structure of the (-)-EGCG , deprotection after the obtained (-)-EGCG this synthetic strategy to avoid lengthy steps through protected in the literature - deprotection , oxidation - reduction method to establish a chiral center . Become a the flavanol compounds the Asymmetric Synthesis common route . In addition, based on the full research and summary of the literature , we explore a synthesis of natural products SFN new green route , compared to the methods used and the literature , more friendly to humans and the environment , avoiding the use of highly toxic chemical reagents , yield much improved at the same time , in line with the atom Principles of Economics . Chapter 3 Reference method reported in gram scale synthesis of the compound 3,6-DCC is optimized , and first reported in the single crystal structure of this compound and its precursor . To fill the gaps in the data of the literature , for intermolecular forces displayed in the crystal structure also gave reasonable resolution . Chapter 4, according to the basis of our research group , the design of novel structure the sulfide Cyclophane 4-1 , and their synthesis discussed strategy for the synthesis reaction is simple and concise route is expected to become a viable route for the synthesis of such compounds .

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