7309-55-9Relevant academic research and scientific papers
A convenient one-pot approach to Paclitaxel (Taxol) side chain via 1,3-dipolar cycloaddition of carbonyl ylides and N-benzoylbenzyl imines
Sheng, Jiajun,Chang, Huan,Qian, Yu,Ma, Mingliang,Hu, Wenhao
supporting information, p. 2141 - 2144 (2018/05/05)
An efficient cascade approach to α-hydroxy-β-amino acid derivatives is reported, which goes through a 1,3-dipolar cycloaddition of carbonyl ylides and N-benzoylbenzyl imines and followed by hydrolysis under acidic conditions. This is the first example of using N-benzoylbenzyl imine as dipolarophile for 1,3-dipolar cycloaddition with carbonyl ylide, which provides a direct and convenient access for the one-pot synthesis of paclitaxel side chain and its derivatives.
An investigation of nitrile transforming enzymes in the chemo-enzymatic synthesis of the taxol sidechain
Wilding, Birgit,Veselá, Alicja B.,Perry, Justin J. B.,Black, Gary W.,Zhang, Meng,Martínková, Ludmila,Klempier, Norbert
supporting information, p. 7803 - 7812 (2015/07/15)
Paclitaxel (taxol) is an antimicrotubule agent widely used in the treatment of cancer. Taxol is prepared in a semisynthetic route by coupling the N-benzoyl-(2R,3S)-3-phenylisoserine sidechain to the baccatin III core structure. Precursors of the taxol sidechain have previously been prepared in chemoenzymatic approaches using acylases, lipases, and reductases, mostly featuring the enantioselective, enzymatic step early in the reaction pathway. Here, nitrile hydrolysing enzymes, namely nitrile hydratases and nitrilases, are investigated for the enzymatic hydrolysis of two different sidechain precursors. Both sidechain precursors, an openchain α-hydroxy-β-amino nitrile and a cyanodihydrooxazole, are suitable for coupling to baccatin III directly after the enzymatic step. An extensive set of nitrilases and nitrile hydratases was screened towards their activity and selectivity in the hydrolysis of two taxol sidechain precursors and their epimers. A number of nitrilases and nitrile hydratases converted both sidechain precursors and their epimers.
A practical and stereoselective synthesis of taxol side chain
Zhou, Zhongqiang,Mei, Xingguo
, p. 723 - 728 (2007/10/03)
Apractical and efficient synthesis of taxol C-13 side chain from cheap and easily available starting material is described.
Totally stereocontrolled nitrone-ketene acetal based synthesis of (2S,3S)-N-benzoyl-and N-boc-phenylisoserine
Jost,Gimbert,Greene
, p. 6672 - 6677 (2007/10/03)
A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N- benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.
Reduction and resolution methods for the preparation of compounds useful as intemediates for preparing taxanes
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, (2008/06/13)
Reduction and resolution methods for the preparation of compounds useful as intermediates in the preparation of taxanes, and particularly for preparation of desired stereoisomers for use in the formation of the C-13 sidechain of pharmaceutically useful taxanes such as paclitaxel.
Semisynthese von Taxol: eine hochenantio- und -diastereoselektive Synthese der Seitenkette und eine neue Methode zur Esterbildung an C13 unter Verwendung von Thioestern
Gennari, Cesare,Vulpetti, Anna,Donghi, Monica,Mongelli, Nicola,Vanotti, Ermes
, p. 1809 - 1812 (2007/10/03)
Keywords: Asymmetrische Synthesen; Enolate; Imine; Taxol; Thioester
Synthesis of α-hydroxy-β-amino acids from chiral cyanohydrins
Warmerdam, Erwin G.J.C.,Van Rijn, Rachel D.,Brussee, Johannes,Kruse, Chris G.,Van Der Gen, Arne
, p. 1723 - 1732 (2007/10/03)
(-)-(R,E)-2-hydroxy-3-pentenenitrile 1, obtained by R-oxynitrilase catalyzed addition of HCN to 2-butenal, was shown to be an excellent chiral starting material for the synthesis of α-hydroxy-β-amino acids of high enantiomeric and diastereomeric purity. T
