132201-32-2Relevant academic research and scientific papers
Improved large-scale synthesis of phenylisoserine and the taxol C-13 side chain
Voronkov, Michael V.,Gontcharov, Alexander V.,Wang, Zhi-Min
, p. 407 - 409 (2003)
Dihydrodihydroxycinnamic acids and their esters react with acetonitrile or benzonitrile in the presence of sulfuric acid to afford the corresponding syn-β-amino-α-hydroxypropionic acid derivatives. High yields and diastereoselectivity of this transformation allows preparation of various phenylisoserine derivatives on a practical scale.
Novel chemo-enzymatic route to a key intermediate for the taxol side-chain through enantioselective O-acylation. Unexpected acyl migration
Forró, Eniko,Galla, Zsolt,Nádasdi, Zala,árva, Judit,Fül?p, Ferenc
, p. 101 - 105 (2015)
A new enzymatic strategy has been devised for the preparation of a key intermediate for the taxol side-chain from N-hydroxymethylated cis-3-acetoxy-4-phenylazetidin-2-one. Burkholderia cepacia (PS-IM)-catalyzed acylation of the primary OH group with an excess of vinyl butyrate (10 equiv.) furnished the corresponding diester and unreacted monoester with excellent enantiomeric excess values (ee ≥ 98%). Traces of undesirable enantiomeric diacetylated product and diol due to intramolecular acyl migration (～6% mole fractions) were also detected. Finally, (2R,3S)-3-phenylisoserine hydrochloride (ee = 99%), a key intermediate for the taxol side-chain, was prepared from the corresponding diester enantiomer through acidic hydrolysis.
Synthesis method of phenyl isoserine hydrochloride and intermediate thereof (by machine translation)
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Paragraph 0046; 0057-0060, (2020/04/02)
The invention provides a method .for synthesizing phenyl isoserine hydrochloride and an intermediate thereof, II of the compound shown in formula, in the presence of a catalyst: and the method comprises the following steps, synthesizing paclitaxel and docetaxel in the following steps: synthesizing paclitaxel and docetaxel as shown in the following reaction I as shown, in the following steps: II, synthesizing paclitaxel and docetaxel in a low price . and synthesizing the paclitaxel and docetaxel in an inexpensive manner . The invention provides cheap chiral side chain raw material, for synthesizing paclitaxel and, docetaxel as shown in the following step: [,] The present invention provides cheap chiral side. chain raw materials. (by machine translation)
A new enzymatic strategy for the preparation of (2R,3S)-3-phenylisoserine: a key intermediate for the Taxol side chain
Forro, Eniko,Fueloep, Ferenc
scheme or table, p. 637 - 639 (2010/08/03)
Burkholderia cepacia lipase PS-IM catalysed the hydrolysis of racemic ethyl 3-amino-3-phenyl-2-hydroxypropionate with excellent enantioselectivity (E >200), when the reaction was performed with added H2O as a nucleophile, in iPr2O, at 50 °C. The hydrolysis of the less reactive enantiomeric ethyl 3-amino-3-phenyl-2-hydroxypropionate with 18% HCl afforded the corresponding enantiomerically pure (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid hydrochloride, a key intermediate for the Taxol side chain.
Preparation of β-amino-α-mercapto acids and amides: Stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine
Lee, Sang-Hyeup,Qi, Xin,Yoon, Juyoung,Nakamura, Kensuke,Lee, Yoon-Sik
, p. 2777 - 2787 (2007/10/03)
Stereoselective syntheses of both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine as coupling-ready reagents via the ring-opening reactions of trans- and cis-oxazoline-5-carboxylates with thiolacetic acid were demonstrated. In addition, we report upon ring-opening reactions of oxazoline-5-carboxamides. Ab initio molecular calculations were used to explain the different reactivities of these oxazolines with respect to the ring-opening reaction.
Process for the production β-amino-α-hydroxycarboxylic acids and derivatives thereof
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, (2008/06/13)
Disclosed is a process for producing β-amino-α-hydroxycarboxylic acid derivatives of general formula (2R,3S)- or (2S,3E)-N-(X,Y)-3-amino-2-hydroxy-3-phenyl propionic acid-Z of Formula I, STR1 e.g. of (2E,3S)-3-amino-2-hydroxy-3-phenyl propionic acid or (2R,3S)-N-benzoyl-3-amino-2-hydroxy-3-phenyl propionic acid methylester. Compounds of type I are valuable intermediates in the total synthesis of Taxols which can be used in the treatment of various forms of cancer.
New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method
Ojima, Iwao,Habus, Ivan,Zhao, Mangzhu,Zucco, Martine,Park, Young Hoon,Sun, Chung Ming,Brigaud, Thierry
, p. 6985 - 7012 (2007/10/02)
Highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenyl-isoserine and its analogs. (3R,4S)-N-benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone readily derived from the 3-hydroxy-4-phenyl-β-lactam is coupled with protected baccatin IIIs, followed by deprotection to give optically pure taxol and 10-deacetyl-7,10-bis(Troc)-taxol in good yields. Fully assigned 1H, 13C, and 2D (COSY and HETCOR) NMR spectra of taxol thus synthesized are shown and discussed.
