Category: 171877-39-7

Shi, Min; Jiang, Jian-Kang published the artcile< Synthesis of novel chiral Cu or Ag/S,N cluster complexes and absolute stereostructures as determined by X-ray crystallography>, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione, the main research area is copper silver chiral thiazolidinethione ligand complex preparation structure; crystal structure copper silver chiral thiazolidinethione ligand complex.

Novel chiral Cu(I) and Ag(I) metal complexes were synthesized from the reaction of chiral (S)-(-)-4-benzyl-1,3-thiazolidine-2-thione ligand with CuCl and AgOAc in CH2Cl2 in the presence of Et3N and DMAP at room temperature Their unique crystal structures were determined by x-ray anal. Four Cu(I) atoms and four 1,3-thiazolidine-2-thione ligands form a butterfly-type metal cluster. Six Ag(I) atoms and six 1,3-thiazolidine-2-thione ligands form another butterfly-type cluster.

Chirality published new progress about Crystal structure. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Wu, Yikang; Shen, Xin; Yang, Yong-Qing; Hu, Qi; Huang, Jia-Hui published the artcile< Enantioselective Total Synthesis of (+)-Brefeldin A and 7-epi-Brefeldin A>, Category: thiazole, the main research area is asym synthesis brefeldin a epibrefeldin stereoselective aldol chiral auxiliary; chiral auxiliary oxazolidinone thiazolidinethione stereoselective aldol reaction protecting group; stereoselective reduction elimination solvent effect asym synthesis brefeldin a; intramol Mukaiyama aldol condensation stereoselective Michael asym synthesis brefeldin.

A convergent enantioselective route to brefeldin A (I) and 7-epi-BFA was developed. The key C-4/C-5 chiral centers were established by using chiral auxiliary induced intermol. asym. aldolization in the presence of TiCl4 and TMEDA. The results with the thiazolidinethione/TiCl4 mediated intermol. asym. aldolization added some new information about the scope and limitations to the existing knowledge of that type of reactions (which so far was essentially limited to the reactions with N-propionyl thiazolidinethiones). During the course a method for protecting the liable aldol hydroxyl groups by using inexpensive TBSCl in DMF with 2,6-lutidine as the base was developed to replace the otherwise unavoidable TBSOTf procedure. Due to the excessive steric hindrance, removal of the auxiliary was much more difficult than most literature cases. Cleavage of the oxazolidinone by reduction was almost impossible. The thiazolidinethione auxiliary was relatively easier to remove. However, several reactions reported for facile removal of thiazolidinethione auxiliaries in the literature still failed. Reductive removal of the thiazolidinethione auxiliary was most effectively realized with LiBH4 in di-Et ether in the presence of 1 equiv of MeOH (a modification of a literature procedure for removal of oxazolidinone auxiliaries in less hindered substrates). Apart from the auxiliary removal, oxidation of the alc. into aldehyde and the deprotection of the dithiolane protecting group were also rather difficult in the present context. A range of methods were screened before final solutions were found. The five-membered ring was constructed by employing an intramol. Mukaiyama reaction after many attempts with the intramol. aldolization under a variety of conditions failed. The rate of elimination of the alkoxyl to form the α,β-double bond of a key intermediate cyclopentenone with DBU was highly solvent dependent (very sluggish in CH2Cl2 but rather fast in MeOH). Introduction of the lower chain (which was synthesized by using a Jacobsen KHR to establish the C-15 chirality) was achieved through a Michael addition similar to the precedents in the literature. It has not been noticed before that the yield of this Michael reaction could be dramatically raised by using 3 equiv of the copper-lithium reagent. Reduction of the C-7 carbonyl was apparently more difficult than similar cases in the literature. After examination of many reagents under various conditions, it was found that the best reagent for yielding the α-isomer was (S)-2-methyl-CBS-borolidine/BH3 and that for the β-isomer was L-Selectride. The α- and β-isomers were then further elaborated into (+)-brefeldin A and 7-epi-BFA, resp. An unexpected yet very interesting solubility difference between BFA and 7-epi-BFA was also observed

Journal of Organic Chemistry published new progress about Aldol condensation, stereoselective. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Category: thiazole.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Evans, David A.; Downey, C. Wade; Shaw, Jared T.; Tedrow, Jason S. published the artcile< Magnesium Halide-Catalyzed Anti-Aldol Reactions of Chiral N-Acylthiazolidinethiones>, Category: thiazole, the main research area is acylthiazolidinethione aldehyde anti aldol condensation; aldol condensation catalyst magnesium halide; alc stereoselective preparation.

Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the anti diastereomer, e.g., I. This reaction is catalyzed by 10% MgBr2·OEt2 in the presence of triethylamine and chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes.

Organic Letters published new progress about Alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Category: thiazole.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Minor-Villar, Leticia; Tello-Aburto, Rodolfo; Olivo, Horacio F.; Fuentes, Aydee; Romero-Ortega, Moises published the artcile< Desulfurization-oxygenation of chiral 1,3-thiazolidine-2-thiones and 1,3-oxazolidine-2-thiones using propylene oxide and microwave irradiation>, COA of Formula: C10H11NS2, the main research area is desulfurization oxygenation chiral thiazolidinethione oxazolidinethione propylene oxide microwave; thiazolidinone preparation; oxazolidinone preparation.

An efficient method for the desulfurization-oxygenation of 1,3-thiazolidine-2-thiones and 1,3-oxazolidine-2-thiones using propylene oxide and employing microwave irradiation is described. This strategy of oxygenation of the thiocarbonyl group provides an attractive methodol. to prepare chiral 1,3-thiazolidin-2-ones and 1,3-oxazolidin-2-ones from the corresponding precursors in good yields.

Synlett published new progress about Desulfurization. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, COA of Formula: C10H11NS2.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Oishi, Shunsuke; Saito, Susumu published the artcile< Double Molecular Recognition with Aminoorganoboron Complexes: Selective Alcoholysis of β-Dicarbonyl Derivatives>, Application In Synthesis of 171877-39-7, the main research area is mol recognition aminoorganoboron complex chemoselective regioselective alcoholysis dicarbonyl derivative.

Aminoorganoboron (AOB) complexes recognize alc. and β-dicarbonyl units, and thereby facilitate chemo- and site-selective alcoholysis of the latter. The complex activates both reaction partners. This strategy enables C-C, C-N, and C-O bond cleavage in addition/elimination reactions under near neutral pH conditions and provides a new method for functional group conversions.

Angewandte Chemie, International Edition published new progress about 1,3-Dicarbonyl compounds Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Application In Synthesis of 171877-39-7.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Abe, Hideki; Hikichi, Takuma; Emori, Kosuke; Yokosuka, Akihito; Mimaki, Yoshihiro; Kobayashi, Toyoharu; Ito, Hisanaka published the artcile< Total Synthesis of Catunaregin and Preliminary Evaluation of Its Antitumor Activity>, Reference of 171877-39-7, the main research area is catunaregin synthesis antitumor.

The total synthesis of catunaregin in both racemic and optically active forms was accomplished. The enantioselective synthesis uses the Evans aldol strategy, with an oxazolidinone or thiazolidinethione as the chiral auxiliary. The key features include a syn-selective aldol reaction to form the Evans-syn or non-Evans-syn product, and a successive ketalization reaction of a furanyl diol derivative under acidic conditions. The biol. properties of the synthetic racemate and both enantiomers were evaluated against A549 and HL-60 human cancer cells.

European Journal of Organic Chemistry published new progress about Aldol addition, stereoselective. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Reference of 171877-39-7.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Yu, Jeongjae; Armstrong, Daniel W.; Ryoo, Jae Jeong published the artcile< Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations>, Quality Control of 171877-39-7, the main research area is chiral HPLC stationary phase synthesis peptide coupling amino acid; phenylglycinol phenylglycine leucine phenyl amide HPLC stationary phase silica; HPLC enantioseparation aromatic compound; (R)-phenylglycine; (S)-leucine; (S)-leucinol; C3 symmetry; HPLC; N-phenyl amide; chiral stationary phases.

We recently reported a new C3-sym. (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatog. (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-sym. 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-sym. CSPs (CSP 2-CSP 4).

Chirality published new progress about Amino acids Role: RCT (Reactant), RACT (Reactant or Reagent). 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Quality Control of 171877-39-7.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Peixoto, Philippe A.; Severin, Rene; Tseng, Chih-Chung; Chen, David Y.-K. published the artcile< Formal Asymmetric Synthesis of Echinopine A and B>, Product Details of C10H11NS2, the main research area is echinopine sesquiterpene enantioselective formal synthesis cyclization palladium catalyst; Diels Alder reaction echinopine sesquiterpene enantioselective formal synthesis.

The asym. formal synthesis of (+)-echinopines A and B was accomplished. Particularly noteworthy were the cascade construction of the [5,6,7]tricyclic ring system I (R = SiMe2CMe3) from the acyclic enyne precursor (2Z,6R,7R)-H2C:CHCH(CH2CH2CH:CH2)CH(OSiMe2CMe3)(CH2)2CH:CHCO2Me through a palladium-catalyzed cycloisomerization with subsequent intramol. Diels-Alder reaction, and the strategic application of a late-stage ring contraction of epoxy ketone II (R = SiMe2CMe3).

Angewandte Chemie, International Edition published new progress about Cyclization. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Product Details of C10H11NS2.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Huang, Gaochao; Shrestha, Ruben; Jia, Kaimin; Geisbrecht, Brian V.; Li, Ping published the artcile< Enantioselective Synthesis of Dilignol Model Compounds and Their Stereodiscrimination Study with a Dye-Decolorizing Peroxidase>, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione, the main research area is dilignol model compound enantioselective preparation surface plasmon resonance TcDyP.

A four-step enantioselective approach was developed to synthesize anti (1R,2S)-I and (1S,2R)-I containing a β-O-4 linkage in good yields. A significant difference was observed for the apparent binding affinities of four stereospecific lignin model compounds with TcDyP by surface plasmon resonance, which was not translated into a significant difference in enzyme activities. The discrepancy may be attributed to the conformational change involving a loop widely present in DyPs upon H2O2 binding.

Organic Letters published new progress about Diastereoselective synthesis. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Sanichar, Randy; Carroll, Ciaran; Kimmis, Ryan; Reiz, Bela; Vederas, John C. published the artcile< Dess-Martin periodinane oxidative rearrangement for preparation of α-keto thioesters>, Application In Synthesis of 171877-39-7, the main research area is Dess Martin periodinane oxidative rearrangement alpha keto thioester preparation; keto thioester preparation oxidation beta hydroxy thioester.

A Dess-Martin Periodinane (DMP) mediated oxidative rearrangement reaction was uncovered. The reaction proceeds via oxidation of a β-hydroxy thioester to a β-keto thioester, followed by an α-hydroxylation and then further oxidation to form a vicinal thioester tricarbonyl. This product then rearranges, extruding CO2, to form an α-keto product. The mechanism of the rearrangement was elucidated using 13C labeling and anal. of the intermediates as well as the products of the reaction. This efficient process allows for easy preparation of α-keto thioesters which are potential intermediates in the synthesis of pharmaceutically important heterocyclic scaffolds such as quinoxalinones.

Organic & Biomolecular Chemistry published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Application In Synthesis of 171877-39-7.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica