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The synthesis of (R)-1,3-butanediol (BDO) from its racemate was studied using whole cells of recombinant Escherichia coli expressing an (S)-specific secondary alcohol dehydrogenase (CpSADH) from Candida parapsilosis by enantioselective oxidation. Under the optimized conditions, the yield of (R)-1,3-BDO reached 72.6 g/l, with a molar recovery yield of 48.4% from a racemate of 15% and an optical purity of 95% ee.

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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 cis- and trans-2-methyl-2-oxo-2-trityl-1,3,2-dioxaphosphorinanes were obtained in the Arbuzov reaction of 2-methoxy-4-methyl-1,3,2-dioxaphosphorinane with trityl chloride. The NMR spectra (1H, 13C and 31P) in solution indicated that trans isomer exists in the form of two noncongruent molecules and it adopts two different conformations: a halfchair and a sofa, while the cis isomer exists as the mixed half/chair-sofa conformer. The compounds crystallise as a pure chiral forms and as a racemates. The solid state structural studies show that NMR data are consistent with the single crystal X-ray analysis, but the conformation existing in the crystal structure is more complex than it can be supposed on sole NMR determination. Crystal data: cis-isomer chiral form: space group P32, a = 8.782, b = 8.782, c = 21.680, alpha = 90.00, beta = 90.00, gamma = 120.00, V = 1448.0; cis-isomer racemate: space group Pca21, a = 16.773, b = 8.491, c = 27.006, alpha = 90.00, beta = 90.00, gamma = 90.00, V = 3846.2; trans-isomer racemate: space group Cc, a = 16.133, b = 8.388, c = 16.158, alpha = 90.00, beta = 117.20, gamma = 90.00, V = 1944.8; trans-isomer chiral form: space group P 1, a = 8.397, b = 9.003, c = 14.944, alpha = 80.76, beta = 74.38, gamma = 63.31, V = 971.1).

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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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beta-Galactosyl transfer from lactose to acceptor alcohols (R)-(-)-butan-2-ol, (RS)-butan-2-ol, (S)-(+)-propane-1,2-diol, (RS)-propane-1,2-diol, (S)-(+)-butane-1,3-diol, (RS)-butane-1,3-diol, propane-1,3-diol, (S)-(+)-isopropylideneglycerol (1,2-O-isopropylidene-sn-glycerol) and (RS)-isopropylideneglycerol (rac-1,2-O-isopropylideneglycerol) was studied, catalysed by the beta-galactosidase (beta-D-galactoside galactohydrolase EC 3.2.1.23) of Escherichia coli.Preference for galactosyl transfer to the R-enantiomers of chiral alcohols was observed, although selectivity was not pronounced.Higher selectivity for transfer to the primary hydroxy groups of the primary-secondary diols was observed.The results are interpreted in terms of a proposed active site model for the enzyme.

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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 series of chiral beta3-aminoxy acids or amides with various side chains have been synthesized via two different approaches. One is the Arndt-Eistert homologation approach, using chiral alpha-aminoxy acids as starting materials. The other approach, utilizing the enantioselective reduction of beta-keto esters catalyzed by baker’s yeast or chiral Ru(II) complexes, produces chiral beta3-aminoxy acids with nonproteinaceous side chains. The oligomers of beta3-aminoxy acids can be readily prepared using EDCI/HOAt as the coupling reagent.

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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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(Equation presented) Dibutylboron triflate/diisopropylethylamine mediated aldol-type cyclization provides an expedient route for the stereoselective synthesis of cyclic ethers in a single step. The method is highly efficient for the stereoselective synthesis of 4-cis-tetrahydropyranones. The reaction is proposed to proceed via an SN1-type mechanism through a chair-like transition state, in which both substituents occupy equatorial positions.

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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 number of ether- and thioether-substituted ferrocenes (1,1?-bis(1,3-dioxane-2-yl)ferrocene 1, 1,1?-bis(5-methyl-1,3- dioxane-2-yl)ferrocene 2, 1,1?-bis(4-methyl-1,3-dioxane-2-yl)ferrocene 3, 1,1?-bis[(R)-(-)-4-methyl-1,3-dioxane-2-yl]ferrocene 4, 1,1?-bis(4,6-dimethyl-1,3-dioxane-2-yl)ferrocene 5, and 1,1?-bis(1,3-dithiane-2-yl)ferrocene 6) were synthesised by direct condensation of 1,1?-diformylferrocene with the corresponding diols or dithiols. The crystal structures of 1, 5a, 5b, and 6 were determined by X-ray diffraction studies. Electrospray ionisation mass spectrometry was used to investigate the binding behaviour of 1 and 6 toward alkali as well as transition metal cations. The dioxane-containing species 1 showed high affinity toward Li+ and Na+, whereas the dithiane derivative 6 bound, as expected, preferentially to Hg2+. The Royal Society of Chemistry 2003.

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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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Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. HPLC of Formula: C4H10O2, Name is (S)-Butane-1,3-diol. In a document type is Article, introducing its new discovery., HPLC of Formula: C4H10O2

Mild and sweet: The title reaction proceeds under mild conditions with high regio- and diastereoselectivity (see scheme, PG=protecting group, DiPPF=1,1?-bis(diisopropylphosphino)ferrocene). This reaction is suitable for a wide range of glycal-derived gamma-ketone esters and affords C-glycosides with exclusive beta-selectivity. The method was further applied to a concise formal synthesis of aspergillideA. Copyright

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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 3-step synthesis of the title compound from (S)-aspartic acid is described. The overall yield of this process is 65% and the enantiomeric purity (ep) of the product is greater than 99%.

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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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Marine-derived species, in particular, fungi, algae, sponges, and coelenterates are fertile grounds for the discovery of biologically and pharmacologically potent compounds. These molecules are structurally unique and possess a wide range of pharmacological activities. The rigid spiroacetal framework, that is, tetrahydro-spirofurofuranones is present in cephalosporolides E, F, H, and I, while the macrolactone structure is exemplified by cephalosporolides B, C, D, G, and J. These marine-derived molecular architectures are appealing to the synthetic community for their stereoselective synthesis. The present review represents a comprehensive overview of all the reported syntheses of these marine-derived molecules.

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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 application relates to novel substituted piperidines of the general formula (I) in which R1, R2, R3, R 4, W, X, Z, m and n are each as defined in detail in the description, to a process for their preparation and to the use of these compounds as medicines, in particular as renin inhibitors.

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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