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Enantiomeric recognition of amino acid salts by macrocyclic crown ethers derived from enantiomerically pure 1,8,9,16-tetrahydroxytetraphenylenes

Asymmetric synthesis of (R,R)- and (S,S)-1,8,9,16- tetrahydroxytetraphenylenes was achieved from starting material (2R,3R)-butane-2,3-diol and (2S,3S)-butane-2,3-diol respectively by utilizing a center-to-axis strategy. A series of crown ether compounds 20, 24, and 25 and their corresponding enantiomers derived from chiral tetrahydroxytetraphenylene were synthesized in enantiomerically pure forms. Enantiomeric recognition properties of these hosts toward l- and d-amino acid methyl ester hydrochloride were studied by the UV spectroscopy titration. The tetramer hosts (S,S,S,S,S,S,S,S)-20 and (R,R,R,R,R,R,R,R)-20 exhibited the best enantioselectivities toward l- and d-alanine methyl ester hydrochloride salt with KL/KD = 4.1 and KD/KL = 3.9, respectively. The new chiral macrocyclic hosts would further enrich the host-guest chemistry.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Can You Really Do Chemisty Experiments About (S)-Propane-1,2-diol

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Stereocontrolled Reduction of 2-Acyl-1,3-oxathiane Derivatives by Zn(BH4)2 and YCl3-NaBH4

Both enantiomers of 1,2-alkanediols were prepared by the diastereocontrolled reduction of ketones containing (R)-6-methyl-1,3-oxathiane moiety as a chiral auxiliary; reduction with Zn(BH4)2 selected one diastereoface to give one diastereomer and that with YCl3-NaBH4 produced another diastereomer selectively.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Archives for Chemistry Experiments of (2S,3S)-Butane-2,3-diol

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Effect of Methyl Substitution on Conformation and Molecular Arrangement of BEDT-TTF Derivatives in the Crystalline Environment

Two methylated bis(ethylenedithio)tetrathiafulvalene (ET) derivatives, Me2ET and Me4ET were stereoselectively synthesized to examine the effect of methylation on conformations of dihydrodithiin rings and molecular arrangements in the crystalline state.Since the donating ability of Me2ET and Me4ET are similar to that of ET, the methylated ET derivatives are considered to be appropriate to investigate the “lattice pressure” effect on ET radical salts by changing the volume of donor molecules.The upper limit of an activation energy for the ring inversion of the dimethylated dihydrodithiin in solution was estimated to be 32 kJ mol-1 by 13C NMR spectroscopy.The X-ray structure analyses revealed that orientations of methyl groups are fixed to axial in Me2ET and to equatorial in Me4ET, accompanied by the change of molecular stacking.The “volume of a methyl group” was evaluated by comparing the molecular volumes of Me2ET and Me4ET with that of ET, and the effective volume for the axial methyl group turns out to be 15percent larger than that of the equatorial.The solid state 13C NMR (CP/MAS) spectra of ET and its derivatives showed that the chemical shifts of resonance lines reflect the conformations of dihydrodithiin rings in crystals.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Transition-Metal-Catalyzed Asymmetric Organic Synthesis via Polymer-Attached Optically Active Phosphine Ligands. 6. Asymmetric Hydrogenation with Polymer Catalysts Containing Optically Active Pendent Alcohols

Three acrylate comonomers, (S,S), (R,R) and racemic 1-methyl-2-hydroxypropyl acrylate (7a-c), were prepared from the corresponding isomers of 2,3-butanediol.The acrylates were copolymerized with ethylene dimethacrylate and N-acryloyl-(2S,4S)-4-(diphenylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine (8) to give cross-linked resins containing phosphinopyrrolidines and optically active alcohols.Polymers containing the 4,5-bis<(diphenylphosphino)methyl>-1,3-dioxolane unit (DIOP) were prepared by copolymerizing acrylates 7a-c with ethylene dimethacrylate and 2-p-styryl-4,5-bis<(tosyloxy)methyl>-1,3-dioxolane (1) and treating the polymers with an excess of sodium diphenylphosphide.Exchange of Rh(I) onto these polymers provided catalysts that hydrogenated 2-acetamidoacrylic acid in tetrahydrofuran.The enantiomeric excesses obtained with the polymer-bound catalysts varied with the structure of the pendent alcohol, suggesting the participation of the polymer-bound alcohol at the catalyst site to provide an alcohol-like environment.A difference in enantiomeric excess (ee) was noted when catalysts containing either R or S alcohols were used.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Efficient general synthesis of 1,2- and 1,3-Diols in high enantiomeric excess via the intramolecular asymmetric reduction of the corresponding ketoalkyl diisopinocampheylborinate intermediates

The first successful asymmetric reduction of unhindered aliphatic ketones with B-chlorodiisopinocampheylborane is reported. In contrast to the reduction in high ee of aralkyl ketones, such as acetophenone, with the reagent, the reduction of unhindered dialkyl ketones, such as 3-methyl-2-butanone, provides only poor ee. However, treatment of alpha- and beta-hydroxyketones with one equiv of diisopnocampheylborane or B-chlorodiisopinocampheylborane rapidly produces the corresponding ketoalkyl diisopinocampheylborinate intermediates, which then undergo facile intramolecular reduction. This reaction sequence, followed by oxidative workup, provides a general synthesis of 1,2- and 1,3-diols in 84?99% enantiomeric excess.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Tetrahydrofuran antifungals

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 phosphate ester groups (e.g., a phosphate ester convertible in vivo into a hydroxy group) thereof or a pharmaceutically acceptable salt thereof and pharmaceutical compositions thereof useful for treating and/or preventing fungal infections are disclosed.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Identification and characterization of a mycobacterial NAD+-dependent alcohol dehydrogenase with superior reduction of diacetyl to (S)-acetoin

An enzyme capable of reducing acetoin in the presence of NADH was purified from Mycobacterium sp. B-009, a non-clinical bacterial strain of soil origin. The enzyme is a homotetramer and can be classified as a medium-chain alcohol dehydrogenase/ reductase based on the molecular weight of the monomer. Identification of the structural gene revealed a limited distribution of homologous genes only among actinomycetes. In addition to its activity as a reductase specific for (S)-acetoin (EC 1.1.1.76), the enzyme showed both diacetyl reductase (EC 1.1.1.304) and NAD+ -dependent alcohol dehydrogenase (EC 1.1.1.1) activities. (S)-Acetoin and diacetyl reductases belong to a group of short-chain alcohol dehydrogenase/reductases but do not have superior abilities to dehydrogenate monoalcohols. Thus, the purified enzyme can be readily distinguished from other enzymes. We used the dual functionality of the enzyme to effectively reduce diacetyl to (S)-acetoin, coupled with the oxidation of 1-butanol.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Synthesis of New Optically Active Crown Ethers

Optically active crown ethers 1a-11, 2, 3a,b, 4a,b, 5a,b and the analogue 6 are synthesized.The efficiency of these compounds as phase-transfer catalysts for a series of enantioselective reactions will be tested.This will be described in a following publication. Key Words: Crown ethers, chiral, optically active / Phase transfer catalysts

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Future efforts will undeniably focus on the diversification of the new catalytic transformations. These may comprise an expansion of the substrate scope from aromatic and heteroaromatic compounds to other hydrocarbons. Keep reading other articles of 4254-15-3! Application In Synthesis of (S)-Propane-1,2-diol

A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, Application In Synthesis of (S)-Propane-1,2-diol, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. Application In Synthesis of (S)-Propane-1,2-diol, Name is (S)-Propane-1,2-diol, molecular formula is C3H8O2. In a Patent, authors is £¬once mentioned of Application In Synthesis of (S)-Propane-1,2-diol

PROCESS FOR THE PRODUCTION OF ALKANEDIOL DERIVATIVES

The present invention provides a process for producing an alkanediol derivative represented by the general formula (II) from an ester compound represented by the general formula (I), safely without giving rise to racemization.The present invention lies in a process for producing an alcohol derivative represented by the following general formula (II):(wherein R2and R3are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; X is a hydrogen atom or a protecting group for hydroxyl group; and n is 0 or 1), which process comprises reducing an ester compound represented by the following general formula (I):(wherein R1is an alkyl group having 1 to 4 carbon atoms; and R2, R3, X and n have the same definitions as given above) with sodium borohydride in a mixed solvent of at least one kind of solvent selected from the group consisting of aromatic hydrocarbons, aliphatic hydrocarbons and alicyclic hydrocarbons and a primary alcohol.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Purification and characterization of L-2,3-butanediol dehydrogenase of Brevibacterium saccharolyticum C-1012 expressed in Escherichia coli

The L-2,3-butanediol dehydrogenase produced in E. coli JM109/pLBD2-CTC was purified by 5 steps. The molecular mass of this enzyme was estimated at 110 kDa and the subunit was measured to be 30 KDa. The L-BDH had some differences from the BDHs from other sources in substrate specificity, pI value, pH stability, effects of divalent cations, and organic acids.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate