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Pt/silica modified by cinchonidine and cinchonine is active for the enantioselective hydrogenation of butane-2,3-dione to butane-2,3-diol in dichloromethane at 268-298 K and 10 bar pressure. Reaction proceeds in three stages. In the first, about 85% of the butane-2,3-dione is converted to 3-hydroxybutan-2-one and 15% to three higher molecular weight products by hydrodimerisation. The initial enantiomeric excess in the hydroxybutanone is modest (20 to 40%(R) with cinchonidine as modifier, 10%(S) with cinchonine as modifier) and dependent on the amount of alkaloid used in catalyst preparation. In the second stage, 3-hydroxybutan-2-one is converted to butane-2,3-diol; a marked kinetic effect is observed whereby the minority enantiomer is converted preferentially to butanediol and the enantiomeric excess in the remaining hydroxybutanone increases dramatically to values in the range 62 to 89%(R) and to 30%(S). Under all conditions, the most abundant stereochemical form of the final product is meso-butane-2,3-dione. In the third stage the three dimers are slowly converted by hydrogenation, dissociation, and further hydrogenation to butane-2,3-diol. In the absence of alkaloid, butane-2,3-dione hydrogenation to racemic products in dichloromethane solution proceeds in two distinct stages with no dimer formation. Butane-2,3-dione hydrogenation has also been studied over Pt/silica modified anaerobically by exposure to cinchonidine in ethanol under propyne at 2 bar. This catalyst is remarkably active for the conversion of diketone to diol in ethanol at 293 K and 10 bar and kinetic selection in the second stage of reaction is again observed. The hydrogenation of racemic 3-hydroxybutan-2-one in dichloromethane over cinchonine-modified Pt/silica at 273 K and 10 to 40 bar pressure also showed kinetic selection, an enantiomeric excess of up to 70%(S) appearing in the reactant as it was consumed. Mechanisms which account for these hydrogenations and dimerisations and for the enantioselectivities observed and their variation are presented. This diketone hydrogenation provides an example of consecutive thermodynamic and kinetic control of enantioselectivity in a multistage catalytic reaction.

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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

Chemical Properties and Facts of (2S,3S)-Butane-2,3-diol

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The specification generally relates to compounds of Formula (I): and pharmaceutically acceptable salts and prodrugs thereof, where R1, R4, R5, R6, R7, Linker, X, Y, A, G, D and E have any of the meanings defined herein. This specification also relates to the use of such compounds and pharmaceutically acceptable salts and prodrugs thereof in methods of treatment of the human or animal body, for example in prevention or treatment of cancer. This specification also relates to processes and intermediate compounds involved in the preparation of such compounds and to pharmaceutical compositions containing them.

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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

Brief introduction of (2S,3S)-Butane-2,3-diol

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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

Extracurricular laboratory:new discovery of C4H10O2

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4-Mesyloxypyran-2-ones joined to furan by a three-carbon linker undergo intramolecular-crossed [4+4]-photocycloaddition with high or complete selectivity for the exo cycloadduct. When a C2-symmetric ketal was present on the tether adjacent to the pyranone ring, moderate levels of asymmetric induction were obtained.

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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

Properties and Exciting Facts About (2S,3S)-Butane-2,3-diol

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The present study was undertaken to examine structural features of L- chicoric acid (3) which are important for potency against purified HIV-1 integrase and for reported cytoprotective effects in cell-based systems. Through a progressive series of analogues, it was shown that enantiomeric D- chicoric acid (4) retains inhibitory potency against purified integrase equal to its L-counterpart and further that removal of either one or both carboxylic functionalities results in essentially no loss of inhibitory potency. Additionally, while two caffeoyl moleties are required, attachment of caffeoyl groups to the central linking structure can be achieved via amide or mixed amide/ester linkages. More remarkable is the finding that blockage of the catechol functionality through conversion to tetraacetate esters results in almost no loss of potency, contingent on the presence of at least one carboxyl group on the central linker. Taken as a whole, the work has resulted in the identification of new integrase inhibitors which may be regarded as bis-caffeoyl derivatives of glycidic acid and amino acids such as serine and beta-aminoalanine. The present study also examined the reported ability of chicoric acid to exert cytoprotective effects in HIV-infected cells. It was demonstrated in target and Cell-based assays that the chicotic acids do not significantly inhibit other targets associated with HIV-1 replication, including reverse transcription, protease function, NCp7 zinc finger function, or replication of virus from latently infected cells. In CEM cells, for both the parent chicoric acid and selected analogues, antiviral activity was observable under specific assay conditions and with high dependence on the multiplicity of viral infection. However, against HIV, 1- and HIV-2-infected MT-4 cells, the chicoric acids and their tetraacetylated esters exhibited antiviral activity (50% effective concentration (EC50) ranging from 1.7 to 20 muM and 50% inhibitory concentration (IC50) ranging from 40 to 60 muM).

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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

Top Picks: new discover of C4H10O2

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We have developed a new sulfenylation reagent, 3-phenylsulfenyl-2-(N- cyanoimino)thiazolidine 3, that is readily available and stable upon storage. Compound 3 easily reacts with amines or thiols to give the corresponding sulfenamides or asymmetrical disulfides in excellent yields. It was also found that the alpha-sulfenylation reaction of carbonyl compounds with 3 proceeds smoothly. Furthermore, optically active 4-diphenylmethyl derivative 4 was synthesized as an asymmetric sulfenylation reagent, which realized 96% e.e. upon alpha-sulfenylation of a cyclic beta-keto ester.

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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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Each of the chiral 1,2- and 1,3-diols examined was derivatized exclusively to a single diastereomeric acetal by the use of a new axially chiral reagent, 2?-methoxy-1,1?-binaphthalene-8-carbaldehyde (MBC). The absolute configuration of the original 1,2- and 1,3-diols was determined by the NOE correlation between the proton signals of the reagent moiety and those of the diol moiety in the acetals.

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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

Final Thoughts on Chemistry for (2S,3S)-Butane-2,3-diol

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Reduction of malonaldehyde bis(ethylene and propylene acetals) with borane or monochloroborane produces diether diols 1 and 2 in high yield. Similar reduction of glyoxal his(ethylene acetals) has only limited utility for the preparation of tetrasubstituted triethylene glycols 3. Organotin chemistry is complementary: stannylene acetals prepared from disubstituted vicinal diols can be alkylated with half an equivalent of 1,2-dibromoethane to produce tetrasubstituted triethylene glycols 3, or with two equivalents of 2-chloroethanol to produce disubstituted triethylene glycols 4.

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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

Discovery of (2S,3S)-Butane-2,3-diol

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Wines produced from Baga native variety from the Portuguese Bairrada Appellation, harvest 2000, were submitted to a liquid-liquid continuous extraction with dichloromethane and analysis by gas chromatography-mass spectrometry (GC-MS). A total of 53 compounds were identified and quantified. This wine has 225 mg l-1 volatile compounds, which include aliphatic and aromatic alcohols (44%), acids (27%), esters (15%), lactones (6%), amides (5%), and phenols (1%). To achieve the identification of the major would-be impact odourants, the aroma index was calculated using the concentration of each volatile component and the corresponding odour threshold reported in the literature. This methodology proved suitable, as a preliminary step, for the determination of the would-be impact odourants of Baga wine. From the 53 compounds identified, nine were determined as the most powerful odourants: guaiacol, 3-methylbutanoic acid, 4-ethoxycarbonyl-gamma-butyrolactone, isobutyric acid, 2-phenylethanol, gamma-nonalactone, octanoic acid, ethyl octanoate and 4-(1-hydroxyethyl)-gamma-butyrolactone. These data suggest Baga wine as a fruity-type product with an aroma correlated to a restricted number of compounds.

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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 compound represented by the formula I STR1 wherein X is independently both F or both Cl or one X is independently F and the other is independently Cl; R1 is a straight or branched chain (C3 to C8) alkyl group substituted by one or two hydroxy moieties, an ether or ester thereof (e.g., a polyether ester, heterocyclic ester amino acid ester or phosphate ester) thereof and the carbon with the asterisk (*) has the R or S absolute configuration or a pharmaceutically acceptable salt thereof and pharmaceutical compositions thereof useful for treating and/or preventing fungal infections are disclosed.

A reaction mechanism is the microscopic path by which reactants are transformed into products. Each step is an elementary reaction. In my other articles, you can also check out more blogs about 19132-06-0

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