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This invention relates to several novel methods of manufacturing thromboxane A2 inhibiting 7-[3-alpha-[1-[[(phenylamino)-thioxomethyl]hydrazono]ethyl]-bicyclo[2.2.1]-heptenoic acids.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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A comparative study of the transesterification of five representative chiral and achiral boronic esters with various structurally modified diols was undertaken to qualitatively understand the factors influencing the relative stability of these boronic esters. Several factors such as chelation, conformation, steric bulk of the substituents, size of the heterocycle, and entropy influence the relative rate of transesterification as well as the stability of the boronic esters. Amongst these boronic esters, pinanediol phenylboronic ester was found to be the most stable boronic ester whereas DIPT boronic ester appeared to be thermodynamically the least stable one. The transesterification with sterically hindered diols was observed to be relatively slow, but afforded thermodynamically more stable boronic esters. Boronic esters derived from cis-cyclopentanediols and the bicyclo[2.2.1]heptane-exo,exo-2,3- diols are relatively more stable. This study not only presents the qualitative picture of relative stability of various boronic esters, but also provides helpful hints regarding the possible recovery of chiral auxiliaries. Many C 2-symmetric chiral auxiliaries, such as 2,3-butanediol, 2,4-pentanediol, DIPT, and cis-cyclohexane-1,2-diol, can be retrieved by simple transesterification of the corresponding boronic esters with commercial inexpensive diols, such as pinacol, 1,3-propanediol, and neopentyl glycol.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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A chimeric (2S, 3S)-butanediol dehydrogenase (cLBDH) was engineered to have the strict (S)-configuration specificity of the (2S, 3S)-BDH (BsLBDH) derived from Brevibacterium saccharolyticum as well as the enzymatic stability of the (2R, 3S)-BDH (KpMBDH) from Klebsiella pneumonia by swapping the domains of two native BDHs. However, while cLBDH possesses the stability, it lacks the specificity. In order to assist in the design a BDH having strict substrate specificity, an X-ray structural analysis of a cLBDH crystal was conducted at 1.58 A. The results obtained show some readily apparent differences around the active sites of cLBDH and BsLBDH. Based on this structural information, a novel (2S, 3S)-BDH having a preferred specificity was developed by introducing a V254L mutation into cLBDH. The influence of this mutation on the stability of cLBDH was not evaluated. Nevertheless, the technique described herein is an effective method for the production of a tailor-made BDH.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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C2-Symmetric P-(2-X-aryl)-2,5-dialkylphospholanes (X = dioxolan-2-yl or dioxan-2-yl), designed on the basis of a working model for asymmetric induction, are effective ligands for the Ni(II)-catalyzed asymmetric hydrovinylation of styrenes. Excellent yields (>99%), selectivities for the desired 3-arylbutenes (>99%), high S/C ratios (>1200), and ee’s (up to 91%) have been realized for a number of prototypical vinylarenes. In the dioxolane series, the selectivity depends on the configuration of the C 4 and C5 carbons.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Alkenyl copper – BF3 reagents, associated with tributylphosphine, react stereoselectively with chiral alpha, beta-ethylenic acetals.A precursor of the California Red scale pheromone has been prepared.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The title compounds 6 have been prepared from rac. 1,4-dihydroxytricyclo<6.4.0.04,9>dodecane-7,10-dione (1).In this way the diastereomeric thioacetals 3 made from (-)-(R,R)-2,3-butanedithiol (2) could be separated by chromatography as well as was transformed into the pure enantiomers of 6. (S)-configuration was predicted for (-)-1 from its positive CD at 300 nm.This could be proved by X-ray diffraction analysis with abnormal dispersion of the diastereoisomer of 3 with the smaller RF value, which yields (-)-1 on hydrolysis.The relatively high rotation = 30 of6is explained by steric twisting.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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We have previously reported that Ricinus communis is a good candidate for the phytoremediation of Cd- and Zn-contaminated soil and for fuel production. In this study, changes in the activity of antioxidant enzymes (superoxide dismutase, SOD; catalase, CAT; and guaiacol peroxidase, POD) and the contents of chlorophyll and malondialdehyde (MDA) in R. communis leaves under Cu, Zn, and Cd stress were examined. Compounds from the exudate of R. communis roots were collected and analyzed using GC-MS chromatograms. The results of enzyme activity showed that Cd treatment significantly increased the SOD content of R. communis leaves and slightly elevated the CAT content, whereas the POD content increased markedly at low Cd treatment concentrations and decreased as Cd concentrations increased. Zn treatment distinctly elevated SOD and POD content in R. communis leaves but had no great influence on CAT content. Cu treatment slightly increased CAT activity, while Cu did not evidently change SOD and POD activity. We found 17, 29, 18, 18, and 33 different compounds in the R. communis root exudates from the control group and Cd, Cu, Zn, and Cd+Cu+Zn treatment groups, respectively. The root exudates mainly included ester, alcohol, ether, amide, acid, phenol, alkanes, ketone, aromatic hydrocarbon, and nitrile compounds. However, the root exudates of R. communis grown in uncontaminated soils were dominated by esters, alcohols, and ethers. Single Cu or Zn treatment slightly changed the root exudates, which were dominated by esters, alcohols, and amides. In the Cd and Cd+Cu+Zn treatment groups, the compositions of root exudates apparently increased, with alkanes as the major species (> 88%).

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Provided are a method for treating a saccharide solution, which comprises subjecting a saccharide solution containing at least one selected from the group consisting of a carbonyl compound and an unsaturated alcohol other than a saccharide to hydrogenation reaction to hydrogenate the carbonyl compound and/or the unsaturated alcohol contained in the saccharide solution, a hydrogenated saccharide solution obtained by treating with the treatment method, and a method for producing an organic compound having a process of obtaining the organic compound by acting a microorganism having an organic material producing ability on an organic raw material containing the hydrogenated saccharide solution.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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A practical synthesis of (+)-aklavinone, the aglycone of antitumor antibiotic aclacinomycin A, is achieved by using the asymmetric aldol reaction of 6a to 10a as the key step.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Tin(IV) chloride and titanium(IV) chloride mediated cyclizations of the ortho-allyl-substituted homochiral hydroxyanthraquinone acetals (7)-(10), prepared by optimized reductive Claisen rearrangements, have afforded monochloro and dichloro tetracyclic products, the stereochemistry of which has been assigned by using n.m.r. techniques.An SN2-like process in which the dioxolan ring is maintained as an ion pair intermediate is favoured when either tin(IV) chloride or titanium(IV) chloride is used at -78 deg.Thereafter the direction of addition of chloride at C9 is largely governed by the orientation of this ion pair.An alternative path which probably involves a free oxocarbenium ion predominates at higher temperatures.An adjacent methoxy group on the anthraquinone lowers the stereoselectivity at both C7 and C9, possibly by bidentate coordination of the Lewis acid involving the quinone carbonyl, the methoxy oxygen and the acetal oxygens.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate