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Stereoselective synthesis of protectin D1: A potent anti-inflammatory and proresolving lipid mediator

A convergent stereoselective synthesis of the potent anti-inflammatory, proresolving and neuroprotective lipid mediator protectin D1 (2) has been achieved in 15% yield over eight steps. The key features were a stereocontrolled Evans-aldol reaction with Nagao’s chiral auxiliary and a highly selective Lindlar reduction of internal alkyne 23, allowing the sensitive conjugated E,E,Z-triene to be introduced late in the preparation of 2. The UV and LC/MS-MS data of synthetic protectin D1 (2) matched those obtained from endogenously produced material.

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Computed Properties of C9H9NS2, Name is (S)-4-Phenylthiazolidine-2-thione, belongs to thiazolidine compound, is a common compound. Computed Properties of C9H9NS2In an article, authors is Deng, Xiaobing, once mentioned the new application about Computed Properties of C9H9NS2.

A convenient synthesis of thiazolidin-2-ones from thiazolidine-2-thiones: Antibiotic activity and revisiting the mechanism

Various substituted thiazolidin-2-ones were synthesized from the corresponding thiazolidine-2-thiones with bromoethanol in ethanol with sodium ethoxide as a base. The optimal reaction conditions and mechanism were reinvestigated in detail. The bioassay indicated that (S)-4-isobutyl and (S)-4-benzylthiazolidin-2-ones show certain inhibitive activities against Candida albicans and Escherichia coli. Supplemental materials are available for this article. Go to the publisher’s online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

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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, 185137-29-5, name is (S)-4-Phenylthiazolidine-2-thione, introducing its new discovery. Quality Control of (S)-4-Phenylthiazolidine-2-thione

On the influence of chiral auxiliaries in the stereoselective cross-coupling reactions of titanium enolates and acetals

Titanium enolates from chiral N-propanoyl-1,3-thiazolidine-2-thiones containing bulky substituents at C4 turned out to be excellent platforms to get highly stereocontrolled cross-coupling reactions with acetals. Related oxazolidinethiones also afforded good results, but the corresponding oxazolidinones resulted completely unselective for such reactions, which proves that an exocyclic C{double bond, long}S bond is essential to attain a synthetically useful stereocontrol.

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Stereoselective synthesis of maresin 1

Maresin 1 is a potent anti-inflammatory and pro-resolving lipid mediator derived from docosahexaenoic acid. The total synthesis of maresin 1 is achieved in 10 steps and in 7% overall yield. The Evans-Nagao aldol reaction between (2E,4E)-5-bromopenta-2,4-dienal and different chiral auxiliaries is investigated. The reported synthesis is efficient and highly stereoselective, affording multi-milligram quantities of this biologically interesting lipid mediator.

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Synthetic Route of 185137-29-5, 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, Synthetic Route of 185137-29-5, name is (S)-4-Phenylthiazolidine-2-thione, introducing its new discovery.

A process for preparing ealy grewe department his method (by machine translation)

The invention discloses a […] his preparation method. Ealy grewe department he a kind of effective specific glucose ceramide synthase inhibitor, can be used for treating I treat Gaucher spear. The invention provides a method for synthesizing […] he, the preparation method comprises: 1, 4 – benzodioxane – 6 – formaldehyde with a chiral ligand generating diastereoselective Aldol reaction, of after the reduction reaction, and then by the substitution and Staudinger reaction, then by the amidation reaction ealy grewe department he. The method raw materials are easy, simple operation, high yield and purity, and is easy for industrial production. (by machine translation)

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Regio- and stereoselective synthesis of 1,4-dihydropyridines by way of an intramolecular interaction of a thiocarbonyl or carbonyl with a pyridinium nucleus

Chiral 1,4-dihydropyridines were prepared by the regio- and stereoselective addition of ketene silyl acetals and organometallic reagents to pyridinium salts. In the addition reaction, an intramolecular interaction between the thiocarbonyl or carbonyl with the pyridinium nucleus plays an important role in bringing about the selectivities. The absolute configuration of the newly produced stereogenic center of the 1,4-dihydropyridines was determined by X-ray analysis and CD Cotton effects after conversion into the appropriate derivatives. The working model for the stereoselectivity was proposed based on the ab initio calculations at the RHF/3-21G* level.

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Stereochemical control on the Michael addition of chiral 1,3-oxazolidine-2-thiones to N-crotonyl 1,3-oxazolidin-2-ones

Addition of both antipodes of 4-phenyl 1,3-oxazolidine-2-thione to 4-substituted N-crotonyl 1,3-oxazolidin-2-ones furnished Michael addition products. A perfect match occurred when both Michael donor and acceptor possessed the same stereochemistry and a mismatch when they had opposite stereochemistries. The newly created stereochemical center was shown to be governed by the Michael donor and not by the acceptor.

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On the influence of chiral auxiliaries in the stereoselective cross-coupling reactions of titanium enolates and acetals

Titanium enolates from chiral N-propanoyl-1,3-thiazolidine-2-thiones containing bulky substituents at C4 turned out to be excellent platforms to get highly stereocontrolled cross-coupling reactions with acetals. Related oxazolidinethiones also afforded good results, but the corresponding oxazolidinones resulted completely unselective for such reactions, which proves that an exocyclic C{double bond, long}S bond is essential to attain a synthetically useful stereocontrol.

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Conglomerate formation and crystal structure of 4-phenyl-1,3-thiazolidin-2- one

Racemic 4-phenyl-1,3-thiazolidin-2-one (4-PTO) crystallizes in the form of conglomerate. The conglomerate formation has been confirmed by analyzing Weissenberg X-ray photographs and IR, Raman spectra of the racemate and the enantiopure 4-PTO crystals. The crystal structure of 4-PTO has been determined by X-ray diffraction, and the structural features are compared with those of other 4-phenyl-1,3-oxazolidin-2-one derivatives in order to understand the structural factors leading to the conglomerate formation. In 4-PTO crystals, the N-H?O intermolecular hydrogen bonds are formed between the amide groups of neighboring molecules in a homochiral zigzag chain. In addition, the intermolecular S?O close contacts are observed between the thioether and the carbonyl groups in the same chain unit. Moreover, the phenyl groups of homochiral 4-PTO molecules of different chain units take the T-shaped stacking orientation to each other due to the aromatic CH/pi interaction. These structural factors altogether reinforce the homochiral supramolecular assembly of chain structural units in the 4-PTO crystal.

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Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations

We recently reported a new C3-symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation. In this study, three new C3-symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-symmetric CSPs (CSP 2?CSP 4).

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