133319-36-5Relevant articles and documents
Enantioselective Synthesis of L- and D-Isoserine via Asymmetric Hydrogenation of Methyl N-Phthaloyl-3-amino-2-oxopropanoate
Nozaki, Kyoko,Sato, Naomasa,Takaya, Hidemasa
, p. 2179 - 2182 (1993)
L- and D-isoserine were synthesized enantioselectively via asymmetric hydrogenation of 3-amino-2-oxoester 5 catalyzed by Cl.Recrystallization and deprotection of (S)-6 (81percent ee) afforded enantiomerically pure L-isoserine.The enantioface selection by the catalyst was opposite to that observed in asymmetric hydrogenation of other 2-oxoesters, such as methyl phenylglyoxylate and methyl 2-oxocyclohexylacetate.
Novel method for synthesizing N-substituted phthalic anhydride-(S)-isoserine
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Paragraph 0055; 0057; 0060; 0063; 0066; 0069; 0072; 0075, (2018/10/11)
The invention provides a low-cost method for synthesizing N-substituted phthalic anhydride-(S)-isoserine. The method comprises the following two steps: (1) taking (R)-(-)-3-chloro-1,2-propanediol as astarting raw material to carry out a Gabriel reaction with phthalimide to generate an intermediate (S)-2-(2,3-dyhydroxy-propyl)-isoindole-1,3-dione; and (2) oxidizing the primary alcohol groups in the intermediate (S)-2-(2,3-dyhydroxy-propyl)-isoindole-1,3-dione to carboxyl groups by using a water solution of sodium hypochlorite under the catalyst of a nitrogen oxide of tetramethylpiperidine toprepare the N-substituted phthalic anhydride-(S)-isoserine. Through the method, the use of an expensive raw material (S)-isoserine is avoided, the raw materials are cheap and easily available, the cost is low, the product purity is high, the impurity content is low, and the method is a novel process which can realize industrial production.