132201-33-3Relevant academic research and scientific papers
1,3-Dipolar cycloadditions of carbonyl ylides to aldimines: A three-component approach to syn-α-hydroxy-β-amino esters
Torssell, Staffan,Kienle, Marcel,Somfai, Peter
, p. 3096 - 3099 (2005)
(Chemical Equation Presented) A highly diastereoselective Rh II-catalyzed 1,3-dipolar cycloaddition leads to the formation of syn-β-amino alcohols and syn-α-hydroxy-β-amino acids in high yields (see scheme; p-TSA = poro-toluenesulfonic acid, Bn = benzyl). This three-component approach to the addition of metal-associated carbonyl ylides to aldimines was applied to a short enantioselective synthesis of the C13 side chain of taxol.
High-performance liquid chromatographic assay of taxol
Richheimer, Steven L.,Tinnermeier, David M.,Timmons, Daniel W.
, p. 2323 - 2326 (1992)
A reversed-phase high-performance liquid chromatographic (HPLC) method for assaying taxol bulk drug or process samples is described. The method utilizes a commercially available pentafluorophenyl (PFP) packing material that has greater selectivity for taxol and related taxanes than other reversed-phase media tested. The method has been shown to be accurate, linear, precise, specific, and rugged, and can be used to assay the bulk drug and determine its chromatographic purity as well as to assay taxol in process and biomass samples.
Synthesis and biological activity of C-7, C-9 and C-10 modified taxane analogues from 1-deoxybaccatin VI
Cui, Yongmei,Li, Lanlan,Lin, Haixia,Liu, Hongchun,Xie, Chenghu,Zhang, Minmin
, (2020)
A series of C-7, C-9 and C-10 modified taxane analogues were synthesized and their in vitro anticancer activities against three human cancer cell lines: A-549 (human lung cancer cell line), MDA-MB-231 (human breast cancer cell line), A-549/T (human lung c
Concise synthesis of the Taxol side chain and demethoxy-4-epi-cytoxazone via oxazoline formation through intramolecular benzylic substitution of a bis-trichloroacetimidate
Matsushima, Yoshitaka,Orita, Mina
, (2021/05/10)
A concise and efficient method for synthesizing the Taxol side chain via the corresponding oxazoline intermediate was developed. The oxazoline ring is formed via an SN1 mechanism to ensure that the trans-oxazoline stereochemistry is retained. This process was induced by intramolecular benzylic substitution of a 1,2-bis-trichloroacetimidate, which was obtained from a known, enantiomerically pure diol. Demethoxy-4-epi-cytoxazone was also obtained from the intermediary trans-oxazoline 3b.
N-benzoyl phenylisoserine derivative as well as synthesis method and application thereof
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Paragraph 0116-0119, (2019/09/14)
The invention discloses an N-benzoyl phenylisoserine derivative and a synthesis method thereof. N-benzoyl phenylimine, a diazo compound and isopropyl aldehyde are taken as raw materials, a molecular sieve is taken as a water absorbing agent, rhodium aceta
Chiral Manganese Aminopyridine Complexes: the Versatile Catalysts of Chemo- and Stereoselective Oxidations with H2O2
Ottenbacher, Roman V.,Talsi, Evgenii P.,Bryliakov, Konstantin P.
, p. 78 - 90 (2017/10/06)
In the last decade, manganese(II) complexes with N-donor tetradentate aminopyridine ligands emerged as efficient catalysts of enantioselective epoxidation of olefins and direct selective oxidation of C?H groups in complex organic molecules, with environmentally benign oxidant hydrogen peroxide. In this personal account, we summarize the progress of these catalysts with regard to ligands design, structure-reactivity correlations, evaluation of the substrate scope, as well as mechanistic studies, shedding light on the nature of active sites and the mechanisms of selective oxygenations. Several practically promising catalytic syntheses with the aid of Mn aminopyridine catalysts are exemplified.
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.
Economical route for oxidative cleavage of double bond to synthesize taxol side chain
Bhatia, Sumati,Singh, Sukhdev,Kumar, Rajesh,Kumar, Amit,Olsen, Carl E.,Prasad, Ashok K.
, p. 379 - 386 (2013/05/08)
An efficient, economical and industry-friendly methodology has been developed for the synthesis of C-13 side chain of taxol, (2R,3S)-3-benzamido-2- hydroxy-3-phenylpropanoic acid by oxidative cleavage of alkene precursor N-[(1S,2S)-2-(1′-ethoxyethoxy)-1-p
A strategy to synthesize taxol side chain and (-)-epi cytoxazone via chiral Bronsted acid-Rh2(OAc)4 Co-catalyzed enantioselective three-component reactions
Qian, Yu,Xu, Xinfang,Jiang, Liqin,Prajapati, Dipak,Hu, Wenhao
supporting information; experimental part, p. 7483 - 7486 (2011/02/21)
A new approach to synthesize optically active β-amino-α-hydroxyl acid derivatives via chiral Bronsted acid-Rh2(OAc) 4 cocatalyzed three-component reactions of diazo acetates with alcohols and imines is reported. A matched reaction sy
