Category: Tetrahydrofurans

Safety of (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateIn 2017, Amdouni, Hella;Robert, Guillaume;Driowya, Mohsine;Furstoss, Nathan;Metier, Camille;Dubois, Alix;Dufies, Maeva;Zerhouni, Marwa;Orange, Francois;Lacas-Gervais, Sandra;Bougrin, Khalid;Martin, Anthony R.;Auberger, Patrick;Benhida, Rachid published 《In Vitro and in Vivo Evaluation of Fully Substituted (5-(3-Ethoxy-3-oxopropynyl)-4-(ethoxycarbonyl)-1,2,3-triazolyl-glycosides as Original Nucleoside Analogues to Circumvent Resistance in Myeloid Malignancies》. 《Journal of Medicinal Chemistry》published the findings. The article contains the following contents:

A series of nucleoside analogs, e.g. I, bearing a 1,4,5-tri-substituted-1,2,3-triazole aglycon was synthesized using a straightforward click/electrophilic addition or click/oxidative coupling tandem procedures. SAR anal., using cell culture assays, led to the discovery of a series of compounds belonging to the 5-alkynyl-1,2,3-triazole family that exhibits potent antileukemic effects on several hematol. malignancies including chronic myeloid leukemia (CML) and myelodysplastic syndromes (MDS) either sensitive or resistant to their resp. therapy. Compound I also proved efficient in vivo on mice xenografted with SKM1-R MDS cell line. Addnl., some insights in its mode of action revealed that this compound can induce cell death by caspase and autophagy induction. To complete the study, the researchers used (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate (cas: 144490-03-9) .

(2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate(cas:144490-03-9 Safety of (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate) is an isomer of 1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose (T283100) which is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.

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

COA of Formula: C13H18O9In 2011, Pan, Mei-Ying;Hang, Wen;Zhao, Xiao-Jun;Zhao, Hang;Deng, Peng-Chi;Xing, Zhi-Hua;Qing, Yong;He, Yang published 《Janus-type AT nucleosides: synthesis, solid and solution state structures》. 《Organic & Biomolecular Chemistry》published the findings. The article contains the following contents:

Novel Janus-type nucleoside analogs (1a-d) were synthesized. Their pyrimido[4,5-d]pyrimidine base moiety has one face with a bidentate Watson-Crick donor-acceptor (DA) H-bond array of adenine and the other face with an acceptor-donor (AD) H-bond array of thymine. These nucleosides may self-associate through the self-complementary base pair. Indeed, in the solid state, compound 6d displayed a honeycomb-like supramol. structure with tetrameric membered cavities formed through the combination of reverse Watson-Crick base pairs and aromatic stacking, in which the solvent mols. were accommodated. The result of temperature-dependent CD studies showed that the free nucleosides can form higher order chiral structures in aqueous solution And (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate (cas: 144490-03-9) was used in the research process.

(2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate(cas:144490-03-9 COA of Formula: C13H18O9) is an isomer of 1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose (T283100) which is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.

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

Formula: C9H10O3《Synthesis of glycerophospholipid conjugates of cantharidin and its analogues》 was published in 2000. The authors were Zhou, Zheng-Hong;Chen, Ru-Yu, and the article was included in《Synthetic Communications》. The author mentioned the following in the article:

A series of glycerophospholipid conjugates of cantharidin and its analogs were synthesized in a one-pot reaction, using hexaethylphosphorus triamide, activated by a catalytic amount of iodine, as the phosphorylating reagent. The structures of the title compounds were confirmed by ¹H NMR, ³¹P NMR, IR and elemental anal. And (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) was used in the research process.

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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

Csende, Ferenc;Stajer, Geza published 《A convenient reduction of unsaturated bicyclic anhydrides》. The research results were published in《Organic Preparations and Procedures International》 in 1999.COA of Formula: C9H10O3 The article conveys some information:

Bicyclic anhydrides such as I are hydrogenated in 89-98% yields to saturated bicyclic anhydrides such as II by using cyclohexene as a transfer hydrogenation substrate in the presence of palladium on carbon. E.g., I dissolved in THF is treated with 2 equivalent of cyclohexene in the presence of palladium on carbon and refluxed for 8-12 h to give II in 98% yield. The modified procedure avoids the use of flammable reagents such as Raney nickel or mol. hydrogen. The experimental procedure involved many compounds, such as (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.COA of Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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

COA of Formula: C9H10O3In 1996, McCluskey, Adam;Taylor, Cherie;Quinn, Ronald J.;Suganuma, Masami;Fujiki, Hirota published 《Inhibition of protein phosphatase 2A by cantharidin analogs》. 《Bioorganic & Medicinal Chemistry Letters》published the findings. The article contains the following contents:

The syntheses of several cantharidin analogs and their biochem. effects on protein phosphatase 2A are described. Comparison of the PP2A inhibition of these cantharidin analogs has shown that the 7-oxo moiety and the anhydride system contribute to the biochem. activity. The diacid forms of several anhydrides showed reduced inhibition of PP2A. To complete the study, the researchers used (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.COA of Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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

Formula: C9H10O3《Metal-free, regioselective and stereoregular alternating copolymerization of monosubstituted epoxides and tricyclic anhydrides》 was published in 2018. The authors were Ji, He-Yuan;Chen, Xiao-Lu;Wang, Bin;Pan, Li;Li, Yue-Sheng, and the article was included in《Green Chemistry》. The author mentioned the following in the article:

A metal-free, highly regioselective and stereoregular ring-opening alternating copolymerization (ROAC) of monosubstituted epoxides with tricyclic anhydrides remains a challenge in the advancement of polyester synthesis. Herein, we described an effective group of organic dual catalysts for the ROAC, exhibiting a high catalytic activity (the highest TOF = 330 h^-1 at 110°), narrow polydispersity (PDI <1.20) and excellent alternating selectivity (ester >99%) in a controlled manner. The ROAC of a variety of monosubstituted epoxides and tricyclic anhydrides was carried out under mild conditions. Of importance is the fact that highly regioselective insertion of epoxides has been realized by simple and metal-free catalysts in the ROAC, where the highest regioselectivity is up to 98% for aliphatic epoxides and glycidyl ethers at 80°. Styrene oxide bearing electron-withdrawing Ph also showed a good regioselectivity of 78%. Besides, the complete suppression of epimerization and transesterification was achieved even at high conversion for a variety of tricyclic anhydrides. Furthermore, block and gradient copolymers were synthesized by the sequential addition strategy and one-pot terpolymn. Accordingly, a green, regioselective and stereoregular fabrication of functional polyesters was realized for the first time by a metal-free process. The experimental procedure involved many compounds, such as (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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

Besalu-Sala, Pau;Sola, Miquel;Luis, Josep M.;Torrent-Sucarrat, Miquel published 《Fast and Simple Evaluation of the Catalysis and Selectivity Induced by External Electric Fields》 in 2021. The article was appeared in 《ACS Catalysis》. They have made some progress in their research.HPLC of Formula: 14166-28-0 The article mentions the following:

In the oriented external elec.-field-driven catalysis, the reaction rates and the selectivity of chem. reactions can be tuned at will. The activation barriers of chem. reactions within external elec. fields of several strengths and directions can be computationally modeled. However, the calculation of all of the required field-dependent transition states and reactants is computationally demanding, especially for large systems. Herein, we present a method based on the Taylor expansion of the field-dependent energy of the reactants and transition states in terms of their field-free dipole moments and elec. (hyper)polarizabilities. This approach, called field-dependent energy barrier (FDB_β), allows systematic one-dimensional (1D), two-dimensional (2D), and three-dimensional (3D) representations of the activation energy barriers for any strength and direction of the external elec. field. The calculation of the field-dependent FDB_β energy barriers has a computational cost several orders of magnitude lower than the explicit elec. field optimizations, and the errors of the FDB_β barriers are within the range of only 1-2 kcal·mol^-1. The achieved accuracy is sufficient for a fast-screening tool to study and predict potential elec.-field-induced catalysis, regioselectivity, and stereoselectivity. As illustrative examples, four cycloadditions (1,3-dipolar and Diels-Alder) are studied. To complete the study, the researchers used (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.HPLC of Formula: 14166-28-0 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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

Application In Synthesis of (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateIn 2016, Li, Guo-Xing;Morales-Rivera, Christian A.;Wang, Yaxin;Gao, Fang;He, Gang;Liu, Peng;Chen, Gong published 《Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine》. 《Chemical Science》published the findings. The article contains the following contents:

A photoredox-mediated Minisci C-H alkylation reaction of N-heteroarenes with alkyl boronic acids is reported. A broad range of primary and secondary alkyl groups can be efficiently incorporated into various N-heteroarenes using [Ru(bpy)₃]Cl₂ as photocatalyst and acetoxybenziodoxole as oxidant under mild conditions. The reaction exhibits excellent substrate scope and functional group tolerance, and offers a broadly applicable method for late-stage functionalization of complex substrates. Mechanistic experiments and computational studies suggest that an intramolecularly stabilized ortho-iodobenzoyloxy radical intermediate might play a key role in this reaction system. And (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate (cas: 144490-03-9) was used in the research process.

(2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate(cas:144490-03-9 Application In Synthesis of (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate) is an isomer of 1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose (T283100) which is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.

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

COA of Formula: C9H10O3《Nuclear magnetic resonance spectroscopy. Establishment of configuration in Diels-Alder adducts》 was published in 1967. The authors were Sarkis, George Y., and the article was included in《Bulletin of the College of Science, University of Baghdad》. The author mentioned the following in the article:

The presence of the double bond shifted the absorption downfield for both exo- and endo-protons in dehydronorbornyl and norbornyl acids, acid chlorides, anhydrides, and nitriles. The magnitude of this shift is very small for the endo-proton (of the exo-epimer). When both epimers are available, a differentiation can be made by the fact that the exo-protons absorb at lower field than the endo-protons. And (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) was used in the research process.

In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.COA of Formula: C9H10O3 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.

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