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A Study on Asymmetric Synthesis of (S)-isoserine

Author: MaYongGang
Tutor: YangXiangLiang
School: Huazhong University of Science and Technology
Course: Inorganic Chemistry
Keywords: (S) - isoserine β-amino acid Asymmetric Synthesis Gabriel reaction Jacobsen catalyst Hydrolytic kinetic resolution
CLC: TQ464.7
Type: Master's thesis
Year: 2008
Downloads: 102
Quote: 0
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Abstract


With the the asymmetric synthesis technology development , human opponents drug study increasing depth . The huge market demand for chiral drugs led to a growing number of chiral drugs and intermediates synthesized from the laboratory toward industrial production . β-amino acid is a popular attention in recent years a class of chiral intermediates , drugs, synthetic peptide chain, etc. There are a variety of applications . (S) - is a isoserine having the biological activity of α - hydroxy -beta - amino acid , is an important pharmaceutical intermediates . Many reported the (S) - the isoserine synthetic route , catalytic asymmetric synthesis of ( S ) - isoserine : First synthetic Jacobsen catalyst for a variety of applications in asymmetric catalysis with this article , by IR , 1H NMR , 13C NMR and other methods of its structural characterization; Jacobsen catalyst epoxypropionate hydrolytic kinetic resolution to obtain optically active (S) - epoxy - propionate , and by the temperature, catalyst with body , the catalyst concentration , and other factors to optimize the reaction conditions ; Finally, by introducing an amino group with a Gabriel reaction , and use HCl , hydrazine hydrate hydrolysis and hydrazine solution to give (S) - isoserine , with IR , 1H NMR , 13C NMR, MS, elemental analysis and other structures were confirmed by means of the final product . The catalytic asymmetric synthesis of ( S ) - the isoserine the route has a simple, safe , low cost , easy to realize industrialization .

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CLC: > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Drug production of biological products > Amino acids,peptides,proteins
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