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Magnesium Tetraarylporphyrin Tweezer: A CD-Sensitive Host for Absolute Configurational Assignments of alpha-Chiral Carboxylic Acids

A protocol to determine the absolute configuration of alpha-chiral carboxylic acids based on a modified circular dichroic (CD) exciton chirality method has been developed. The protocol relies on a host-guest complexation mechanism: the chiral substrates are derivatized to give bifunctional amide conjugates (“guests”) that form complexes with a dimeric magnesium porphyrin host, Mg-T (T stands for “tweezer”) that acts as a “receptor”. The two porphyrins in the complex adopt a preferred helicity dictated by the substituents at the chiral center in accordance with their steric sizes (assigned on the basis of conformational energy A-values) and, consequently, with the absolute configuration of the substrates under investigation. This chiroptical method, verified with a variety of chiral substrates, has been demonstrated to be reliable and generally applicable, including natural products with complex structures. Molecular modeling, NMR, and FTIR experiments of selected host-guest complexes revealed the mode of ligation of the substrates to the magnesium porphyrin species and led to clarification of the structure of the complex. When oxygen functionalities were directly attached to the chiral center, the signs of the CD couplets were opposite to those predicted on the basis of steric size. NMR and molecular modeling experiments indicated that this apparent inconsistency was due to conformational characteristics of the guest molecules. The stereochemical analysis is shown to be a sensitive technique, not only for the determination of absolute configurations of substrates but also for elucidation of their solution conformations.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Process for preparing optically active tetrahydro-2-furoic acid

A process for preparing an optically active tetrahydro-2-furoic acid is disclosed. The process comprises (i) reacting (¡À)-tetrahydro-2-furoic acid with an optically active amine resolver of the following formula (I): STR1 wherein R1 is a lower alkyl group and R2 represents an alkyl group or ar aryl group, provided that R1 and R2 are different from each other, thus producing an optically active diastereomer salt, and (ii) decomposing the diastereomer salt. According to the process, a high purity, optically active tetrahydro-2-furoic acid can be prepared at a high yield using an amine resolver. The amine resolver can be recovered at a high yield and high purity.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Zirconium(IV)- and hafnium(IV)-catalyzed highly enantioselective epoxidation of homoallylic and bishomoallylic alcohols

In this report, zirconium(IV)- and hafnium(IV)-bishydroxamic acid complexes were utilized in the highly enantioselective epoxidation of homoallylic alcohols and bishomoallylic alcohols, which used to be quite difficult substrates for other types of asymmetric epoxidation reactions. The performance of the catalyst was improved by adding polar additive and molecular sieves. For homoallylic alcohols, the reaction could provide epoxy alcohols in up to 83% yield and up to 98% ee, while, for bishomoallylic alcohols, up to 79% yield and 99% ee of epoxy alcohols rather than cyclized tetrahydrofuran compounds could be obtained in most cases.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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NOVEL DISUBSTITUTED 3,4-DIAMINO-3-CYCLOBUTENE-1,2-DIONE COMPOUNDS FOR USE IN THE TREATMENT OF CHEMOKINE-MEDIATED DISEASES

Disubstituted 3,4-diamino-3-cyclobutene-1,2-dione compounds are described that correspond to general formula (I). Also described, are pharmaceutical compositions that include these compounds and methods of using these compounds and compositions for the treatment of chemokine-mediated diseases.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Electric Literature of 87392-05-0. In my other articles, you can also check out more blogs about 87392-05-0

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Hydroxyethylene sulfones as a new scaffold to address aspartic proteases: Design, synthesis, and structural characterization

Hydroxyethylene sulfones were developed as novel scaffolds against aspartyl proteases. A diastereoselective synthesis has been established to introduce the required side chain decoration with desired stereochemistry. Depending on the substitution of the hydroxyethylene sulfone core, micro- to submicromolar inhibition of HIV-1 protease is achieved for the S-configuration at P 1 and R-configuration at the hydroxy-group-bearing backbone atom. This stereochemical preference is consistent with the S,R configuration of amprenavir. The racemic mixture of the most potent derivative (Ki = 80 nM) was separated by chiral HPLC, revealing the S,R,S-enantiomer to be more active (Ki = 45 nM). Docking studies suggested this isomer as the more active one. The subsequently determined crystal structure with HIV-1 protease, cocrystallized from a racemic mixture, exclusively reveals the S,R,S-enantiomer accommodated to the binding pocket. The transition state mimicking hydroxy group of the inhibitor is centered between both catalytic aspartates, while either its carbonyl or sulfonyl group forms H-bonds to the structurally conserved water mediating interactions between ligand and Ile50NH/Ile50NH? of both flaps. Biological testing of the stereoisomeric hydroxyethylene sulfones against cathepsin D and beta-secretase did not reveal significant inhibition. Most likely, the latter proteases require inverted configuration at the hydroxy group.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 87392-05-0, name is (R)-(+)-2-Tetrahydrofuroic acid, introducing its new discovery. SDS of cas: 87392-05-0

INHIBITING FATTY ACID SYNTHASE (FASN)

The present disclosure is directed to inhibitors of FASN. The compounds can be useful in the treatment of disease or disorders associated with the inhibition of FASN. For instance, the disclosure is concerned with compounds and compositions for inhibition of FASN, methods of treating, preventing, or ameliorating diseases or disorders associated with the inhibition of FASN, and methods of synthesis of these compounds.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Enzyme-triggered enantioconvergent transformation of haloalkyl epoxides

Biocatalytic hydrolysis of 2,3-disubstituted rac-cis- and rac-trans-haloalkyl epoxides 1a-8a using the epoxide hydrolase activity of whole bacterial cells furnished the corresponding vicinal diols 1b-8b as intermediates; these (spontaneously) underwent ring closure to yield cyclic products 1c-6c through an enzyme-triggered cascade reaction. In particular, cis-configured substrates (1a, 3a, 5a, 7a) were transformed in an enantioconvergent fashion, which resulted in the formation of single stereoisomeric products in 100% des and up to 92% ees from the racemates.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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A selenide-based approach to photochemical cleavage of peptide and protein backbones at engineered backbone esters

(Chemical Equation Presented) A strategy for photochemical cleavage of peptide and protein backbones is described, which is based on a selenide-mediated cleavage of a backbone ester moiety. Studies in model systems establish the viability of the chemistry and suggest the method could be a valuable tool for chemical biology studies of proteins.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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CARBONYLAMINO PYRROLOPYRAZOLES, POTENT KINASE INHIBITORS

Carbonylamino Pyrrolopyrazole compounds of formula I, compositions including these compounds and methods of their use are provided. Preferred compounds of formula I have activity as protein kinase inhibitors, including as inhibitors of PAK4.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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87392-05-0,87392-05-0, (R)-(+)-2-Tetrahydrofuroic acid is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of (2R)-tetrahydrofuran-2-carboxylic acid (2 g, 17.22 mmol) in THF (20 mL) was added the BH3. SMe2 (2.58 mL, 25.84 mmol) at 0C, then the mixture was stirred at 20 C for 16 hours to give the colorless solution.. 2N NaOH (10 mL) was added to the mixture slowly at 0 C. Then the mixture was extracted with EtOAc (20 mL x 2). The combined organic phase was washed with brine (10 mL), dried over Na2SC>4, filtered and concentrated to give the crude product (450.00 mg, 4.41 mmol, 26% yield) as colorless oil. *H NMR (CDC13, 400MHz) deltaH = 4.07 – 3.97 (m, 1H), 3.94 – 3.85 (m, 1H), 3.84 – 3.76 (m, 1H), 3.72-3.63 (m, 1H), 3.55 – 3.46 (m, 1H), 2.02 – 1.87 (m, 4H), 1.72 – 1.65 (m, 1H).

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Reference£º
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem