Tag: 200-300

Boryl Radicals Enabled a Three-Step Sequence to Assemble All-Carbon Quaternary Centers from Activated Trichloromethyl Groups was written by Zhao, Qiang;Li, Bin;Zhou, Xi;Wang, Zhao;Zhang, Feng-Lian;Li, Yuanming;Zhou, Xiaoguo;Fu, Yao;Wang, Yi-Feng. And the article was included in Journal of the American Chemical Society in 2022.Synthetic Route of C12H20O6 This article mentions the following:

Here, a straightforward three-step sequence that uses a range of readily accessible activated trichloromethyl groups as the carbon source, the three C-Cl bonds of which were selectively functionalized to introduce three alkyl chains was described. In each step, only a single C-Cl bond was cleaved with the choice of an appropriate Lewis base-boryl radical as the promoter. A vast range of diversely substituted all-carbon quaternary centers could be accessed directly from these activated CCl₃ trichloromethyl groups or by simple derivatizations. The use of different alkene traps in each of the three steps enabled facile collections of a large library of products. The utility of this strategy was demonstrated by the synthesis of variants of two drug mols., whose structures could be easily modulated by varying the alkene partner in each step. The results of kinetic and computational studies enabled the design of the three-step reaction and provided insights into the reaction mechanisms. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Synthetic Route of C12H20O6).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofuran (THF), or oxolane, is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. THF can also be synthesized by catalytic hydrogenation of furan. This allows certain sugars to be converted to THF via acid-catalyzed digestion to furfural and decarbonylation to furan, although this method is not widely practiced. THF is thus derivable from renewable resources.Synthetic Route of C12H20O6

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

Copper-Catalyzed 6-endo-dig Cyclization-Coupling of 2-Bromoaryl Ketones and Terminal Alkynes toward Naphthyl Aryl Ethers in Water was written by Su, Lebin;Xie, Shimin;Dong, Jianyu;Pan, Neng;Yin, Shuang-Feng;Zhou, Yongbo. And the article was included in Organic Letters in 2022.Application In Synthesis of (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol This article mentions the following:

The cyclization-coupling reaction of 2-bromoaryl ketones 2-Br-4-R-5-R¹C₆H₂C(O)Me (R = H, Cl, F, MeO; R¹ = H, Cl, Me), 1-(pyridin-3-yl)ethan-1-one and terminal alkynes R²CCH (R² = Ph, 4-bromophenyl, pyridin-3-yl, etc.) is first realized by copper catalysis, which produces polyfunctional naphthyl aryl ethers I (X = CH, N) in moderate to excellent yields with broad substrate scope and good functional group tolerance. This reaction proceeds via 6-endo-dig cyclization and C(sp²)-O coupling using green H₂O as the unique solvent and 5-bromopyrimidin-2-amine as the critical additive. Mechanistically, a unique Cu(III)-acetylide probably is the key intermediate, which allows exclusive 6-endo-dig selectivity. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Application In Synthesis of (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Solid acid catalysis, and the advantages often associated with their use, have been proved equally efficient for the synthesis of tetrahydrofurans or furans. Tetrahydrofuran can also be produced, or synthesised, via catalytic hydrogenation of furan. This process involves converting certain sugars into THF by digesting to furfural. An alternative to this method is the catalytic hydrogenation of furan with a nickel catalyst.Application In Synthesis of (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

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

Radical Acylation of [1.1.1]Propellane with Aldehydes: Synthesis of Bicyclo[1.1.1]pentane Ketones was written by Li, Qing;Li, Lin;Xu, Qiao-Ling;Pan, Fei. And the article was included in Organic Letters in 2022.Related Products of 582-52-5 This article mentions the following:

Bicyclo[1.1.1]pentanes (BCPs) are widely utilized in drug design as sp³-rich bioisosteres for tert-Bu, internal alkynes, and aryl groups. A general and mild method for radical acylation of [1.1.1]propellane with aldehydes were developed. The protocol provided straightforward access to bicyclo[1.1.1]pentane ketones with a broad substrate scope. The synthetic utility of this methodol. was demonstrated by the late-stage modification of bioactive mols. and the versatile transformation of bicyclo[1.1.1]pentane ketones, making it useful for drug discovery. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Related Products of 582-52-5).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives.Tetrahydrofuran has many industry uses as a solvent including in natural and synthetic resins, high polymers, fat oils, rubber, polymer. Tetrahydrofuran can also be produced, or synthesised, via catalytic hydrogenation of furan. This process involves converting certain sugars into THF by digesting to furfural. An alternative to this method is the catalytic hydrogenation of furan with a nickel catalyst.Related Products of 582-52-5

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

Nascent-HBr-Catalyzed Removal of Orthogonal Protecting Groups in Aqueous Surfactants was written by Gupta, Shilpi;Bera, Smritilekha;Mondal, Dhananjoy. And the article was included in Journal of Organic Chemistry in 2020.Formula: C12H20O6 This article mentions the following:

Organic reactions in the aqueous environment have recently emerged as a promising research area. The generation of nascent-HBr from the slow hydrolysis of the dispersed catalyst, benzyl bromide, with the interior water present in the hydrophobic core of the confined micellar medium in aqueous surfactant is described for the first time. The sustained-release nascent-HBr enabled the chemoselective cleavages of acid-sensitive orthogonal functionalities present in carbohydrates, amino alcs., and hydroxylated acyclic compounds in good to excellent yields. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Formula: C12H20O6).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofuran and dihydrofuran form the basic structural unit of many naturally occurring scaffolds like gambieric acid A and ciguatoxin, goniocin, and some biologically active molecules. THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.Formula: C12H20O6

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

Synthesis and antimicrobial activity of (-)-cleistenolide and analogues was written by Benedekovic, Goran;Popsavin, Mirjana;Radulovic, Niko S.;Stojanovic-Radic, Zorica;Farkas, Sandor;Francuz, Jovana;Popsavin, Velimir. And the article was included in Bioorganic Chemistry in 2021.Reference of 582-52-5 This article mentions the following:

Using the “chiral pool” approach, two modified total syntheses of the biol. active δ-lactone cleistenolide was achieved starting from D-glucose. These approaches also enabled the preparation of novel analogs and derivatives of natural product I. The applied strategy for the synthesis of I involves: the initial degradation of the chiral precursor for a single C-atom, C₂-fragment chain extension using Z-selective Wittig reaction, and the final δ-lactonization. All tested cleistenolide analogs displayed antimicrobial activity against a panel of nine microbial strains, most of them superseding the activity of cleistenolide itself, and, in some cases, coming close in value to the observed minimal inhibitory concentrations of chloramphenicol. Increased lipophilicity of the derivatives and the non-sterically congested conjugated lactone moiety were a prerequisite for analogs with high inhibitory activity against S. aureus and, in general, Gram-pos. bacteria. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Reference of 582-52-5).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. Tetrahydrofuran (THF) is primarily used as a precursor to polymers including for surface coating, adhesives, and printing inks.Reference of 582-52-5

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

Synthesis and Structure-Activity Relationship Studies of C2-Modified Analogs of the Antimycobacterial Natural Product Pyridomycin was written by Kienle, Maryline;Eisenring, Patrick;Stoessel, Barbara;Horlacher, Oliver P.;Hasler, Samuel;van Colen, Gwenaelle;Hartkoorn, Ruben C.;Vocat, Anthony;Cole, Stewart T.;Altmann, Karl-Heinz. And the article was included in Journal of Medicinal Chemistry in 2020.Recommanded Product: 582-52-5 This article mentions the following:

A series of derivatives of the antimycobacterial natural product pyridomycin have been prepared with the C2 side chain attached to the macrocyclic core structure by a C-C single bond, in place of the synthetically more demanding enol ester double bond found in the natural product. Hydrophobic C2 substituents of sufficient size generally provide for potent anti-Mtb activity of these dihydropyridomycins, e.g., I (R = Me, Et, cyclohexyl, CH₂Ph), (min. inhibitory concentration (MIC) values around 2.5μM), with several analogs thus approaching the activity of natural pyridomycin. Surprisingly, some of these compounds, in contrast to pyridomycin, are insensitive to overexpression of InhA in Mycobacterium tuberculosis (Mtb). This indicates that their anti-Mtb activity does not critically depend on the inhibition of InhA and that their overall mode of action may differ from that of the original natural product lead. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Recommanded Product: 582-52-5).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Recommanded Product: 582-52-5

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

Zinc(II) Iodide-Directed β-Mannosylation: Reaction Selectivity, Mode, and Application was written by Zhong, Xuemei;Zhou, Siai;Ao, Jiaming;Guo, Aoxin;Xiao, Qian;Huang, Yan;Zhu, Wanmeng;Cai, Hui;Ishiwata, Akihiro;Ito, Yukishige;Liu, Xue-Wei;Ding, Feiqing. And the article was included in Journal of Organic Chemistry in 2021.SDS of cas: 582-52-5 This article mentions the following:

A direct, efficient, and versatile glycosylation methodol. promises the systematic synthesis of oligosaccharides and glycoconjugates in a streamlined fashion like the synthesis of medium to long-chain nucleotides and peptides. The development of a generally applicable approach for the construction of 1,2-cis-glycosidic bond with controlled stereoselectivity remains a major challenge, especially for the synthesis of β-mannosides. Here, we report a direct mannosylation strategy mediated by ZnI₂, a mild Lewis acid, for the highly stereoselective construction of 1,2-cis-β linkages employing easily accessible 4,6-O-tethered mannosyl trichloroacetimidate donors. The versatility and effectiveness of this strategy were demonstrated with successful β-mannosylation of a wide variety of alc. acceptors, including complex natural products, amino acids, and glycosides. Through iteratively performing ZnI₂-mediated mannosylation with the chitobiosyl azide acceptor followed by site-selective deprotection of the mannosylation product, the novel methodol. enables the modular synthesis of the key intermediate trisaccharide with Man-β-(1→4)-GlcNAc-β-(1→4)-GlcNAc linkage for N-glycan synthesis. Theor. investigations with d. functional theory calculations delved into the mechanistic details of this β-selective mannosylation and elucidated two zinc cations’ essential roles as the activating agent of the donor and the principal mediator of the cis-directing intermol. interaction. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5SDS of cas: 582-52-5).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.SDS of cas: 582-52-5

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

Photoinduced triiodide-mediated [3+2] cycloaddition of N-tosyl aziridines and alkenes was written by Li, Yuanbo;Chen, Fan;Zhu, Shengqing;Chu, Lingling. And the article was included in Organic Chemistry Frontiers in 2021.SDS of cas: 582-52-5 This article mentions the following:

A metal-free photoinduced triiodide-mediated [3+2] cycloaddition of N-Ts aziridines I (R¹ = Ph, 2-naphthyl, 4-fluorophenyl, etc.) with alkenes R²CH=CH₂ (R² = 4-bromophenyl, 2-naphthyl, benzofuran-5-yl, 4-methylthiazol-5-yl, etc.) is described. This operationally simple protocol utilized bench-stable and inexpensive TBAI as a radical mediator, enabling regioselective access to substituted pyrrolidines II with good functional group compatibility. Preliminary mechanistic experiments disclosed that TBAI₃, generated in situ from TBAI, promoted the crucial radical ring-opening of N-Ts aziridines I. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5SDS of cas: 582-52-5).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofuran (THF) is a Lewis base that bonds to a variety of Lewis acids such as I2, phenols, triethylaluminum and bis(hexafluoroacetylacetonato)copper(II). It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.SDS of cas: 582-52-5

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

Synthesis and Structure-Activity Relationship Studies of C2-Modified Analogs of the Antimycobacterial Natural Product Pyridomycin was written by Kienle, Maryline;Eisenring, Patrick;Stoessel, Barbara;Horlacher, Oliver P.;Hasler, Samuel;van Colen, Gwenaelle;Hartkoorn, Ruben C.;Vocat, Anthony;Cole, Stewart T.;Altmann, Karl-Heinz. And the article was included in Journal of Medicinal Chemistry in 2020.Recommanded Product: 582-52-5 This article mentions the following:

A series of derivatives of the antimycobacterial natural product pyridomycin have been prepared with the C2 side chain attached to the macrocyclic core structure by a C-C single bond, in place of the synthetically more demanding enol ester double bond found in the natural product. Hydrophobic C2 substituents of sufficient size generally provide for potent anti-Mtb activity of these dihydropyridomycins, e.g., I (R = Me, Et, cyclohexyl, CH₂Ph), (min. inhibitory concentration (MIC) values around 2.5μM), with several analogs thus approaching the activity of natural pyridomycin. Surprisingly, some of these compounds, in contrast to pyridomycin, are insensitive to overexpression of InhA in Mycobacterium tuberculosis (Mtb). This indicates that their anti-Mtb activity does not critically depend on the inhibition of InhA and that their overall mode of action may differ from that of the original natural product lead. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Recommanded Product: 582-52-5).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Recommanded Product: 582-52-5

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

Zinc(II) Iodide-Directed β-Mannosylation: Reaction Selectivity, Mode, and Application was written by Zhong, Xuemei;Zhou, Siai;Ao, Jiaming;Guo, Aoxin;Xiao, Qian;Huang, Yan;Zhu, Wanmeng;Cai, Hui;Ishiwata, Akihiro;Ito, Yukishige;Liu, Xue-Wei;Ding, Feiqing. And the article was included in Journal of Organic Chemistry in 2021.SDS of cas: 582-52-5 This article mentions the following:

A direct, efficient, and versatile glycosylation methodol. promises the systematic synthesis of oligosaccharides and glycoconjugates in a streamlined fashion like the synthesis of medium to long-chain nucleotides and peptides. The development of a generally applicable approach for the construction of 1,2-cis-glycosidic bond with controlled stereoselectivity remains a major challenge, especially for the synthesis of β-mannosides. Here, we report a direct mannosylation strategy mediated by ZnI₂, a mild Lewis acid, for the highly stereoselective construction of 1,2-cis-β linkages employing easily accessible 4,6-O-tethered mannosyl trichloroacetimidate donors. The versatility and effectiveness of this strategy were demonstrated with successful β-mannosylation of a wide variety of alc. acceptors, including complex natural products, amino acids, and glycosides. Through iteratively performing ZnI₂-mediated mannosylation with the chitobiosyl azide acceptor followed by site-selective deprotection of the mannosylation product, the novel methodol. enables the modular synthesis of the key intermediate trisaccharide with Man-β-(1→4)-GlcNAc-β-(1→4)-GlcNAc linkage for N-glycan synthesis. Theor. investigations with d. functional theory calculations delved into the mechanistic details of this β-selective mannosylation and elucidated two zinc cations’ essential roles as the activating agent of the donor and the principal mediator of the cis-directing intermol. interaction. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5SDS of cas: 582-52-5).

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.SDS of cas: 582-52-5

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