Category: 171877-39-7

Crimmins, Michael T. published the artcileSynthesis and diastereoselective aldol reactions of a thiazolidinethione chiral auxiliary, Application In Synthesis of 171877-39-7, the main research area is thiazolidinethione chiral auxiliary; propanoyl thiazolidinethione syn aldol.

Thiazolidinethione chiral auxiliary I (R = H) is prepared from (S)-phenylalaninol and carbon disulfide. Propanoylated I [R = C(O)CH2CH3] can be used for either Evans syn aldol reactions or non-Evans syn aldol reactions with a variety of aldehydes, in good yield with good stereoselectivity.

Organic Syntheses published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 171877-39-7 belongs to class thiazole, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, Application In Synthesis of 171877-39-7.

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

Sanichar, Randy published the artcileDess-Martin periodinane oxidative rearrangement for preparation of α-keto thioesters, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione, 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, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione.

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

Baiget, Jessica published the artcileOn the influence of chiral auxiliaries in the stereoselective cross-coupling reactions of titanium enolates and acetals, Safety of (S)-4-Benzylthiazolidine-2-thione, the main research area is acylthiazolidinethione titanium enolate coupling acetal.

Titanium enolates from chiral N-propanoyl-1,3-thiazolidine-2-thiones containing bulky substituents at C-4 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 were completely unselective for such reactions, which proves that an exocyclic C=S bond is essential to attain a synthetically useful stereocontrol.

Tetrahedron published new progress about Acetals Role: RCT (Reactant), RACT (Reactant or Reagent). 171877-39-7 belongs to class thiazole, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, Safety of (S)-4-Benzylthiazolidine-2-thione.

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

Crimmins, Michael T.; Azman, Adam M. published the artcile< A modular, stereoselective approach to spiroketal synthesis>, Computed Properties of 171877-39-7, the main research area is modular stereoselective synthesis spiroketal milbemycin fragment.

A highly convergent and flexible synthetic approach to stereochem. defined spiroketals is reported. Substituents can be incorporated at various positions around the spiroketal framework without significant disruption to the synthetic scheme. The approach has been exploited to prepare the spiroketal fragment of milbemycin β14.

Synlett published new progress about Aldehydes 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, Computed Properties of 171877-39-7.

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

Michaelis, Lars; Schinzer, Dieter published the artcile< Studies toward the total synthesis of sorangicins: a shortened synthesis of the dioxabicyclo[3.2.1]octane core>, Application In Synthesis of 171877-39-7, the main research area is sorangicin preparation antibiotic antibacterial agent.

An access to the dioxabicyclo[3.2.1]octane core of 6-methyl-8-(3,3a,8,9,10,11,12,13,14,15,18,19,22,23,25,26,28,34a-octadecahydro-11,14,15-trihydroxy-10,38-dimethyl-28-oxo-9,13-epoxy-23,26-etheno-2,5-methano-2H,5H-furo[2,3-l][1,4,14]trioxacyclotritriacontin-25-yl)-7-nonenoic acid [i.e., (+)-sorangicin A] was developed, using a keto lactone formation, a Mukaiyama-Michael reaction and an epoxide opening as the key steps. The synthesis of the target compound was achieved using (4S)-4-(phenylmethyl)-2-thiazolidinethione as a chiral auxiliary. The title compound thus formed was (8E)-2,5:3,7-dianhydro-4,6,8,9-tetradeoxy-6-methyl-9-phenyl-L-glycero-L-gluco-non-8-enitol, (8E)-2,5:3,7-dianhydro-4,6,8,9-tetradeoxy-6-methyl-9-phenyl-L-glycero-L-gluco-non-8-enose.

Synlett published new progress about Antibacterial agents. 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

Chen, Ning; Jia, Weiyi; Xu, Jiaxi published the artcile< A Versatile Synthesis of Various Substituted Taurines from Vicinal Amino Alcohols and Aziridines>, Related Products of 171877-39-7, the main research area is taurine substituted preparation amino alc aziridine carbon disulfide; oxidation thiazolidinethione.

Taurine and structurally diverse substituted taurines have been synthesized by peroxyformic acid oxidation of the thiazolidine-2-thione intermediates generated from vicinal amino alcs. or aziridines and carbon disulfide. The stereochem. and mechanisms of the reactions are discussed. The method is a salt-free and versatile route, convenient in terms of purification, and can be used to synthesize optically active substituted taurines. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009).

European Journal of Organic Chemistry published new progress about Amino alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Related Products of 171877-39-7.

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

Lu, Cuifen; Nie, Junqi; Yang, Guichun; Chen, Zuxing published the artcile< An improved synthesis of sitophilure>, Category: thiazole, the main research area is asym synthesis sitophilure aldol reaction chiral auxiliary.

The asym. synthesis of sitophilure (I) was carried out in 8 steps, with 42% overall yield and 97% enantiomeric excess from propionaldehyde. The synthesis relied on an approach employing an asym. acyl-thiazolidinethione propionate aldol reaction to establish two stereogenic centers.

Canadian Journal of 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

Kitir, Betul; Baldry, Mara; Ingmer, Hanne; Olsen, Christian A. published the artcile< Total synthesis and structural validation of cyclodepsipeptides solonamide A and B>, Name: (S)-4-Benzylthiazolidine-2-thione, the main research area is cyclodepsipeptide solonamide A B total enantioselective synthesis antimicrobial; macrocycle virulence gene expression Staphylococcus aureus inhibitor cyclodepsipeptide; hydroxy acid stereoselective aldol reaction esterification acylation macrolactamization.

Microorganisms are an attractive source of new natural products with antimicrobial properties, and the marine environment constitutes a prolific resource of bioactive microorganisms. During a global research expedition (Galathea III), two depsipeptides, solonamide A and solonamide B, were isolated from the marine bacterium Photobacterium halotolerance and were found to inhibit virulence gene expression in the serious human pathogen, Staphylococcus aureus. They act by interfering with the agr quorum sensing system and show resemblance to the endogenous S. aureus quorum sensing peptide, autoinducing peptide I (AIP-I). To enable more comprehensive studies, we embarked on the chem. synthesis of solonamides A and B. The key synthetic steps were formation of the (R)-β-hydroxy-fatty-acids by stereoselective aldol reactions and a cyclative macrolactamization, which proceeded under highly dilute conditions. Thus, the first total syntheses of the solonamides corroborated the originally assigned structures, and by changing the stereochem. of the auxiliary in the aldol steps we gained access to the natural products as well as their β3-epimers.

Tetrahedron published new progress about Acylation. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Name: (S)-4-Benzylthiazolidine-2-thione.

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

Wu, Yikang; Sun, Ya-Ping; Yang, Yong-Qing; Hu, Qi; Zhang, Qi published the artcile< Removal of thiazolidinethione auxiliaries with benzyl alcohol mediated by DMAP. [Erratum to document cited in CA141:295695]>, SDS of cas: 171877-39-7, the main research area is erratum acylthiazolidinethione benzyl alc substitution DMAP; benzyl ester preparation erratum; DMAP substitution mediator erratum.

All of the starting thiazolidine-thiones (compounds 1, 1′, 3, 5, 7, 9, 11, 13, 13′, 15, 17, 19, 21, 23, 27, and 29) are yellow oils, not colorless ones.

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

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

Sparrow, Kevin John; Carley, Sarah; Sohnel, Tilo; Barker, David; Brimble, Margaret A. published the artcile< Studies towards development of asymmetric double-Mannich reactions of chiral 2-oxocyclohexanecarboxylate derivatives with bis(aminol)ethers>, Related Products of 171877-39-7, the main research area is azabicyclooctanecarboxylic acid imide ester preparation; nonracemic oxazolidinone imide ester oxocyclohexanecarboxylic acid preparation Mannich reaction; erbium lanthanum catalyst double Mannich reaction oxocyclohexanecarboxylate aminol ether; double Mannich reaction nonracemic oxazolidinone imide ester oxocyclohexanecarboxylic acid; azabicyclooctanecarbonyl methylphenyloxazolidinone mol crystal structure.

An improved method for the double-Mannich reaction of β-ketoesters and bis(aminol)ethers (EtOCH2)2NR (R = Et, PhCH2) in the presence of Er(OTf)3 or La(OTf)3 was developed. Esters of 2-oxocyclohexanecarboxylic acid with 8-phenylmenthol, pantolactone, and trans-2-phenylcyclohexanol and imides with norephedrine-, (S)-phenylalaninol-, and (S)-α,α-diphenylvalinol-derived oxazolidinones and oxazolidinethiones were prepared Double Mannich reaction of EtN(CH2OEt)2 with the oxocyclohexanecarboxylic acid esters and imides yielded mixtures of azabicyclooctanecarboxylic acid ester and imide diastereomers. The oxocyclohexanecarboxylic acid imide with a norephedrine-derived oxazolidinone and its derived azabicyclooctanecarboxylic acid imide product were separated into their diastereomers; the structures of both reactant imide diastereomers and the major azabicyclooctanecarboxylic acid imide diastereomer were assigned by X-ray crystallog.

Tetrahedron published new progress about Chiral auxiliary. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Related Products of 171877-39-7.

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