Category: Tetrahydrofurans

Synthesis of Sugar and Nucleoside Analogs and Evaluation of Their Anticancer and Analgesic Potentials was written by Hussain, Fahad;Rahman, Fahad Imtiaz;Saha, Poushali;Mikami, Atsushi;Osawa, Takashi;Obika, Satoshi;Rahman, S. M. Abdur. And the article was included in Molecules 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:

Chem. modification of sugars and nucleosides has a long history of producing compounds with improved selectivity and efficacy. In this study, several modified sugars (2-3) and ribonucleoside analogs (4-8) have been synthesized from α-d-glucose in a total of 21 steps. The compounds were tested for peripheral anti-nociceptive characteristics in the acetic acid-induced writhing assay in mice, where compounds 2, 7, and 8 showed a significant reduction in the number of writhes by 56%, 62%, and 63%, resp. The compounds were also tested for their cytotoxic potential against human HeLa cell line via trypan blue dye exclusion test followed by cell counting kit-8 (CCK-8) assay. Compound 6 demonstrated significant cytotoxic activity with an IC₅₀ value of 54 μg/mL. Mol. docking simulations revealed that compounds 2, 7, and 8 had a comparable binding affinity to cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) enzymes. Addnl., the bridged nucleoside analogs 7 and 8 potently inhibited adenosine kinase enzyme as well, which indicates an alternate mechanistic pathway behind their anti-nociceptive action. Cytotoxic compound 6 demonstrated strong docking with cancer drug targets human cytidine deaminase, proto-oncogene tyrosine-protein kinase Src, human thymidine kinase 1, human thymidylate synthase, and human adenosine deaminase 2. This is the first ever reporting of the synthesis and analgesic property of compound 8 and the cytotoxic potential of compound 6. 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. THF (Tetrahydrofuran) is water-miscible and has a low viscosity making it a highly versatile solvent used in a variety of industries. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.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

Optimization and Validation of an HPAEC-PAD Method for the Quantification of FODMAPs in Cereals and Cereal-Based Products was written by Ispiryan, Lilit;Heitmann, Mareile;Hoehnel, Andrea;Zannini, Emmanuele;Arendt, Elke K.. And the article was included in Journal of Agricultural and Food Chemistry in 2019.Product Details of 470-69-9 This article mentions the following:

This study presents an anal. method for the quantification of fermentable oligo-, di-, and monosaccharides and polyols (FODMAPs) in cereals and cereal-based products, considering diverse ingredients, such as different cereals in addition to wheat, pulses, or pseudocereals. All carbohydrates have been separated, identified, and quantified with a high-performance anion-exchange chromatog. system coupled with a pulsed amperometric detection (HPAEC-PAD). The total fructan content and the average d.p. (DP_av) have been determined after enzymic hydrolysis to the monomers glucose and fructose, on the basis of the principle of the official method for fructan quantification in food products, AOAC 997.08. The methods for extraction, separation, and detection as well as fructan determination are based on several other studies and were modified in order to minimize interferences in the anal. The method has been validated with regard to the limits of detection and quantification, the linearity, the repeatability, and the accuracy as well as the DP_av of the fructans. 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: 470-69-9Product Details of 470-69-9).

(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. Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.Product Details of 470-69-9

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

Migration resistant glucose esters as bioplasticizers for polylactide was written by Yang, Xi;Hakkarainen, Minna. And the article was included in Journal of Applied Polymer Science in 2015.Name: (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate This article mentions the following:

Environmental and sustainability issues have catalyzed efforts to replace traditional polymer additives with biobased alternatives. Glucose pentaacetate (GPA) and sucrose octaacetate (SOA) as model com. saccharide esters and three synthesized glucose hexanoate esters (GHs) were evaluated as bioplasticizers for polylactide (PLA). For the GHs different reaction times were utilized to reach plasticizers with different number of hexanoate groups to establish how the degree of substitution influences miscibility and migration resistance of the plasticizers. The synthesized GHs, GPA, and SOA all showed good miscibility with PLA. Largest improvements in strain at break were observed for the PLA films containing GH plasticizers. These films also exhibited simultaneous increase in stress at break as compared to plain PLA. The GH plasticizers had low tendency to migrate during aging in water and this migration resistance increased with increasing degree of substitution. The GHs are, thus, promising plasticizer alternatives for bioplastics as they also retain the biodegradable nature of these biobased materials. © 2015 Wiley Periodicals, Inc. J.Appl.Polym.Sci. 2015, 132, 41928. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (cas: 126-14-7Name: (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate).

(2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (cas: 126-14-7) 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 (THF) is primarily used as a precursor to polymers including for surface coating, adhesives, and printing inks.Name: (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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

Sweet potato-apple snack functionalized with agavins for children′s consumption was written by Garcia Villalba, Wendy Guadalupe;Rodriguez Herrera, Raul;Ochoa Martinez, Luz Araceli;Rutiaga Quinones, Olga Miriam;Cervantes Cardoza, Veronica;Gonzalez Herrera, Silvia Marina. And the article was included in Journal of Food Processing and Preservation in 2021.Recommanded Product: (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 This article mentions the following:

In this study, an orange sweet potato-apple-based snack supplemented with agavins was developed for children′s consumption, in order to obtain a functional product. The consumer acceptability, physicochem., mech. properties, and the presence of flavonoids and phenolic acids were determined using chromatog. coupled to mass spectrometry (UPLC-MS/MS), as well as the carbohydrate profile by thin layer chromatog. (TLC). It was found that the addition of orange sweet potato and the presence of agavins influence the texture of the product. The TLC showed the presence of agavins in the snack and the UPLC-MS/MS showed presence of phenolic acids and flavonoids. The 20% orange sweet potato-80% apple formulation obtained high sensory acceptability, as well as the highest concentration of phenolic acids. The study indicates its potential as a functional food. The presence of agavins pos. modified the mech. properties of the snack, indicating its potential as a texturizing agent, also the snacks are rich in flavonoids and phenolic acids which positions its as a functional food. Technol. it was possible to develop snack based on orange sweet potato-apple, with the presence of agavins and microbiol. stable. 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: 470-69-9Recommanded Product: (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).

(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 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 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.Recommanded Product: (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

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

Deposition of Small Organic Molecules by the Displacement of Two Immiscible Supercritical Phases was written by Kim, Jaehoon;Carbonell, Ruben G.. And the article was included in Langmuir in 2006.Reference of 126-14-7 This article mentions the following:

A new coating process is described (deposition from two immiscible supercritical phases, or DISP) in which a solution of supercritical carbon dioxide (scCO₂) with a desired solute is displaced by supercritical helium (scHe). After depressurization, the solute is deposited on substrates initially submerged in the coating solvent. Micron-sized particles and thin films of sucrose octaacetate (SOA) were formed on silicon wafer substrate coupons from DISP at relatively low temperatures and pressures (≤6500 psi and ≤60 °C). The particle size, film thickness, and morphol. of SOA were characterized as a function of coating conditions-solution concentrations, withdrawal velocities, and pressures. Particles in the range of 1-14 μm in diameter were deposited at low solute concentrations (≤0.2 wt % at 4500 psi), whereas films in the range of 0.1-0.5 μm in thickness were deposited at higher solute concentrations (≥1.5 wt % at 4500 psi). Particle sizes decreased with increasing displacement velocity and increasing pressure. Estimates of characteristic times for diffusion and nucleation indicate that DISP is a diffusion-limited process. Optical microscopy and at. force microscopy (AFM) were used to characterize film morphol., including defect formations and film roughness. Highly uniform films with low root-mean-square (RMS) roughness (∼10 Å) were obtained at a low displacement velocity of 0.0035 cm/s, while ring-like defect structures were observed in films deposited at a higher displacement velocity of 0.035 cm/s. The film thickness and morphol. of the films deposited from DISP were compared with films from normal dip coating with typical organic solvents (acetone and toluene). Films deposited from scCO₂ by DISP were much thicker, more uniform, and exhibited much fewer drying defects and lower RMS roughness compared with films from the organic solvents. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (cas: 126-14-7Reference of 126-14-7).

(2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (cas: 126-14-7) 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. 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.Reference of 126-14-7

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