cas 25613-60-9, Z-L-Phenylalanine N-carboxyanhydride | Articles data ｜lookchem

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25613-60-9

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Practical syntheses of chiral α-amino acids and chiral half-esters by kinetic resolution of urethane-protected α-amino acid N-carboxyanhydrides and desymmetrization of cyclic meso-anhydrides with new modified cinchona alkaloid catalysts
The large-scale applications of the kinetic resolution of urethane-protected α-amino acid N-carboxyanhydrides (UNCAs) and the desymmetrization of cyclic meso-anhydrides using modified cinchona alkaloids are described. These asymmetric reactions are effective organocatalytic methods for the synthesis of chiral a-amino acids 6 and chiral half-esters 2 on an industrial scale, because the organocatalyst recovery and product purification can be carried out by a simple extractive procedure obviating a chromatographic purification step. The modified cinchona alkaloid catalysts (DHQD) 2AQN and (DHQ)2AQN, as reported by Deng and co-workers, are not readily available and therefore not suitable for industrial-scale synthesis. Various O-alkylated quinidine and quinine derivatives were prepared and screened as catalysts for the kinetic resolution of phenylalanine UNCA with alcohol. The readily prepared O-propargylquinidine (OPQD) and O-propargylquinine (OPQ) were discovered to be highly enantioselective and practical catalysts. These new catalysts were applied to the synthesis of chiral propargylglycine 24 and the key intermediate of BAY10-8888/PLD-118, 26, on an industrial scale, by the kinetic resolution of UNCA 22 and the desymmetrization of cyclic meso-anhydride 25, respectively.
Ishii, Yutaka,Fujimoto, Ryosuke,Mikami, Masafumi,Murakami, Satoshi,Miki, Yasushi,Furukawa, Yoshiro
p. 609 - 615
(2012/12/31)

Urethane-protected amino acid N-carboxy anhydrides and their use in peptide synthesis
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Fuller,Cohen,Shabankareh,Blair,Goodman,Naider
p. 7414 - 7416
(2007/10/02)

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Chemical Properties

Melting Point: 108-109 °C
Boiling Point: 451.3±38.0 °C(Predicted)
Density: 1.353±0.06 g/cm3(Predicted)
PKA: -3.09±0.40(Predicted)
PSA: 72.91000
LogP: 2.85120

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