Category: Tetrahydrofurans

Photochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization was written by Campbell, Mark W.;Yuan, Mingbin;Polites, Viktor C.;Gutierrez, Osvaldo;Molander, Gary A.. And the article was included in Journal of the American Chemical Society in 2021.Product Details of 582-52-5 This article mentions the following:

Herein, the implementation of efficient, sustainable, diaryl ketone hydrogen-atom transfer (HAT) catalysis to activate native C-H bonds for multicomponent dicarbofunctionalization of alkenes was reported. The ability to forge new carbon-carbon bonds between reagents typically viewed as commodity solvents provided a new, more atom-economic outlook for organic synthesis. Through detailed exptl. and computational investigation, the critical effect of hydrogen bonding on the reactivity of this transformation was uncovered. 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: 582-52-5Product Details 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. 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.Product Details of 582-52-5

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

A photoinduced transient activating strategy for late-stage chemoselective C(sp³)-H trifluoromethylation of azines was written by Huang, Mengjun;Ma, Jiawei;Zou, Zhenlei;Li, Heyin;Liu, Jiyang;Kong, Lingyu;Pan, Yi;Zhang, Weigang;Liang, Yong;Wang, Yi. And the article was included in Chemical Science in 2022.Reference of 582-52-5 This article mentions the following:

The direct functionalization of C(sp³)-H bonds is an ultimately ideal synthetic strategy with high atom economy and step efficiency. However, the direct trifluoromethylation of electron-deficient heteroaryl adjacent C(sp³)-H bonds remains a formidable challenge. Herein, we describe a transient activating strategy involving a Tf-shift process and π-π stacking interaction for catalyst-free direct benzylic C(sp³)-H trifluoromethylation of azines, e.g., pyridne, pyrimidine, quinoline, dihydropyridinone, tetrahydroisoquinoline, and tetrahydroquinazoline, with an air-stable crystalline imidazolium sulfonate reagent IMDN-Tf. This bench-stable cationic reagent offers a scalable and practical protocol for the late-stage modification of drug mols. with high site selectivity, which avoids the prefunctionalization and the use of stoichiometric metals and strong oxidants. Furthermore, comprehensive mechanistic studies revealed the determining effect of π-π stacking for the activation of azinylic C(sp³)-H bonds. 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. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.Reference of 582-52-5

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

Mechanistic Investigation of 1,2-Diol Dehydration of Paromamine Catalyzed by the Radical S-Adenosyl-L-methionine Enzyme AprD4 was written by Yeh, Yu-Cheng;Kim, Hak Joong;Liu, Hung-wen. And the article was included in Journal of the American Chemical Society in 2021.Formula: C12H20O6 This article mentions the following:

AprD4 is a radical S-adenosyl-L-methionine (SAM) enzyme catalyzing C3′-deoxygenation of paromamine to form 4′-oxo-lividamine. It is the only 1,2-diol dehydratase in the radical SAM enzyme superfamily that has been identified and characterized in vitro. The AprD4 catalyzed 1,2-diol dehydration is a key step in the biosynthesis of several C3′-deoxy-aminoglycosides. While the regiochem. of the hydrogen atom abstraction catalyzed by AprD4 has been established, the mechanism of the subsequent chem. transformation remains not fully understood. To investigate the mechanism, several substrate analogs were synthesized and their fates upon incubation with AprD4 were analyzed. The results support a mechanism involving formation of a ketyl radical intermediate followed by direct elimination of the C3′-hydroxyl group rather than that of a gem-diol intermediate generated via 1,2-migration of the C3′-hydroxyl group to C4′. The stereochem. of hydrogen atom incorporation after radical-mediated dehydration was also established. 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 (THF) is a Lewis base that bonds to a variety of Lewis acids such as I2, phenols, triethylaluminum and bis(hexafluoroacetylacetonato)copper(II). Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.Formula: C12H20O6

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

Nickel-Catalyzed Reductive Csp³-Ge Coupling of Alkyl Bromides with Chlorogermanes was written by Guo, Peng;Pang, Xiaobo;Wang, Ke;Su, Pei-Feng;Pan, Qiu-Quan;Han, Guan-Yu;Shen, Qian;Zhao, Zhen-Zhen;Zhang, Wenhua;Shu, Xing-Zhong. And the article was included in Organic Letters in 2022.COA of Formula: C12H20O6 This article mentions the following:

Reductive cross-coupling provides facile access to organogermanes, but it remains largely unexplored. Herein the authors report a Ni-catalyzed reductive Csp³-Ge coupling of alkyl bromides with chlorogermanes. This work established a new method for producing alkylgermanes. The reaction proceeds under very mild conditions and tolerates various functionalities including ether, alc., alkene, nitrile, amine, ester, phosphonates, amides, ketone, and aldehyde. The application of this method to the modification of bioactive mols. is demonstrated. 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: 582-52-5COA of Formula: 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. THF (Tetrahydrofuran) is water-miscible and has a low viscosity making it a highly versatile solvent used in a variety of industries. THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.COA of Formula: C12H20O6

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

Orthosteric-allosteric dual inhibitors of PfHT1 as selective antimalarial agents was written by Huang, Jian;Yuan, Yafei;Zhao, Na;Pu, Debing;Tang, Qingxuan;Zhang, Shuo;Luo, Shuchen;Yang, Xikang;Wang, Nan;Xiao, Yu;Zhang, Tuan;Liu, Zhuoyi;Sakata-Kato, Tomoyo;Jiang, Xin;Kato, Nobutaka;Yan, Nieng;Yin, Hang. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2021.Recommanded Product: (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:

Artemisinin-resistant malaria parasites have emerged and have been spreading, posing a significant public health challenge. Antimalarial drugs with novel mechanisms of action are therefore urgently needed. In this report, we exploit a ‘selective starvation’ strategy by inhibiting Plasmodium falciparum hexose transporter 1 (PfHT1), the sole hexose transporter in P. falciparum, over human glucose transporter 1 (hGLUT1), providing an alternative approach to fight against multidrug-resistant malaria parasites. The crystal structure of hGLUT3, which shares 80% sequence similarity with hGLUT1, was resolved in complex with C3361, a moderate PfHT1-specific inhibitor, at 2.3-Å resolution Structural comparison between the present hGLUT3-C3361 and our previously reported PfHT1-C3361 confirmed the unique inhibitor binding-induced pocket in PfHT1. We then designed small mols. to simultaneously block the orthosteric and allosteric pockets of PfHT1. Through extensive structure-activity relationship studies, the TH-PF series was identified to selectively inhibit PfHT1 over hGLUT1 and potent against multiple strains of the blood-stage P. falciparum. Our findings shed light on the next-generation chemotherapeutics with a paradigm-shifting structure-based design strategy to simultaneously target the orthosteric and allosteric sites of a transporter. 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: (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. 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. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Recommanded Product: (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

Lipase-catalyzed synthesis of fatty acid esters of trisaccharides was written by Gonzalez-Alfonso, Jose L.;Casas-Godoy, Leticia;Arrizon, Javier;Arrieta-Baez, Daniel;Ballesteros, Antonio O.;Sandoval, Georgina;Plou, Francisco J.. And the article was included in Methods in Molecular Biology (New York, NY, United States) in 2018.Formula: C18H32O16 This article mentions the following:

Carbohydrate fatty acid esters have a broad spectrum of applications in the food, cosmetic, and pharmaceutical industries. The enzyme-catalyzed acylation is significantly more selective than the chem. process and is carried out at milder conditions. Compared with mono- and disaccharides, the acylation of trisaccharides has been less studied. However, trisaccharide esters display notable bioactive properties, probably due to the higher hydrophilicity of the sugar head group. In this chapter, we describe the acylation of two trisaccharides, maltotriose and 1-kestose, catalyzed by different immobilized lipases, using vinyl esters as acyl donors. To illustrate the potential of such compounds, the antitumor activity of 6′′-O-palmitoyl-maltotriose is shown. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 470-69-9Formula: C18H32O16).

(2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 470-69-9) 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. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Formula: C18H32O16

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

Electrophotocatalytic Si-H activation governed by polarity-matching effects was written by Jiang, Yangye;Xu, Kun;Zeng, Chengchu. And the article was included in CCS Chemistry in 2022.Computed Properties of C12H20O6 This article mentions the following:

Trialkylsilanes are important building blocks in organic synthesis; however, their widespread use in redox chem. is limited by their high oxidation potentials and comparably high bond dissociation energies (BDEs) of Si-H and α-Si-C-H bonds (>92 kcal mol-1). Herein, we report a new strategy for Si-H bond homolysis enabled by the synergistic combination of electrooxidation, photoinduced ligand-to-metal charge transfer (LMCT), and radical-mediated hydrogen atom transfer (HAT). Governed by the polarity-matching effect, the HAT to electrophilic MeO· or [Cl-OHCH₃]· from the more hydridic Si-H instead of a C-H bond allows the selective generation of silyl radicals. This electrophotocatalytic protocol provides rapid access to Si-functionalized benzimidazo-fused isoquinolinones with broad functional-group compatibility. Mechanistic studies have shown that n-Bu4NCl is essential to the electrooxidation of CeCl₃ to form the Ce(IV) species. 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: 582-52-5Computed Properties 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. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. 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.Computed Properties of C12H20O6

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

Molecular Construction of Sulfonamide Antisense Oligonucleotides was written by Korotkovs, Valerijs;Reichenbach, Linus F.;Pescheteau, Clementine;Burley, Glenn A.;Liskamp, Rob M. J.. And the article was included in Journal of Organic Chemistry in 2019.Application of 582-52-5 This article mentions the following:

An efficient and scalable synthesis of new oligonucleotide monomers was developed for replacement of the phosphodiester backbone of RNA by a sulfonamide-containing backbone to enable construction of sulfonamide antisense oligonucleotides (SaASOs). It was shown that by employing these sulfonamide RNA (SaRNA) monomers, it was possible to synthesize oligomers in solution The properties of a sulfonamide moiety replacement were evaluated by incorporation of a SaRNA-monomer into a DNA strand and performing thermal stability tests of the resulting DNA and RNA-double-strand hybrids. Although sulfonamide modification caused a decrease in melting temperature (T_m) of both hybrids, it was lower for the sulfonamide-containing DNA-RNA hybrid than that for the sulfonamide-containing DNA-DNA hybrid. 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 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. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. 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.Application of 582-52-5

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

A Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles was written by Goncalves, Carlos R.;Lemmerer, Miran;Teskey, Christopher J.;Adler, Pauline;Kaiser, Daniel;Maryasin, Boris;Gonzalez, Leticia;Maulide, Nuno. And the article was included in Journal of the American Chemical Society in 2019.Formula: C12H20O6 This article mentions the following:

Functionalization at the α-position to carbonyl compounds has classically relied on enolate chem. As a result, generation of a new C-X bond whereby X is more electroneg. than carbon requires an oxidation event. By rendering the α-position of amides electrophilic through a mild and chemoselective Umpolung transformation, a broad range of widely available oxygen, nitrogen, sulfur and halogen nucleophiles can be used to generate α-functionalized amides. Over 60 examples are presented to establish the generality of this process and calculations of the mechanistic aspects underline a fragmentation pathway that accounts for the broadness of this methodol. 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. THF (Tetrahydrofuran) is water-miscible and has a low viscosity making it a highly versatile solvent used in a variety of industries. 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.Formula: C12H20O6

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

Design, synthesis, and biological evaluation of thiazole bioisosteres of goniofufurone through in vitro antiproliferative activity and in vivo toxicity was written by Svircev, Milos;Popsavin, Mirjana;Pavic, Aleksandar;Vasiljevic, Branka;Rodic, Marko V.;Djokic, Sanja;Kesic, Jelena;Sreco Zelenovic, Bojana;Popsavin, Velimir;Kojic, Vesna. And the article was included in Bioorganic Chemistry in 2022.Safety 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 synthesis of several new goniofufurone bioisosteres was achieved in which the Ph residue was replaced by a thiazole ring. The key steps of the synthesis included the initial condensation of cyanohydrin benzoates with cysteine Et ester hydrochloride, followed by the subsequent reaction of resulting C-4′ epimeric thiazolines with DBU, to introduce 5-deoxy functionality and to elaborate the thiazole ring in one step. Synthesized compounds showed potent growth inhibitory effects against selected human tumor cell lines, especially bioisostere 4, which in the culture of MCF-7 cells displayed the highest activity (IC₅₀ = 0.19 nM) of all compounds under evaluation. This mol. exhibited 64474-fold higher antiproliferative activity than lead 2 and was1053-fold more active than the compounds antitumor agent doxorubicin in the culture of MCF-7 cells. The structural features of the tested compounds responsible for their antiproliferative activity have been identified by preliminary SAR anal. The toxicity of the most active compound 4 was assessed by an in vivo experiment in a zebrafish model (Danio rerio), whereupon it was found non-toxic at any of the tested concentrations up to 125 μM. 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: 582-52-5Safety 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.Tetrahydrofuran has many industry uses as a solvent including in natural and synthetic resins, high polymers, fat oils, rubber, polymer. 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.Safety 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