Month: November 2022

Inhibition of Chikungunya virus by an adenosine analog targeting the SAM-dependent nsP1 methyltransferase was written by Mudgal, Rajat;Mahajan, Supreeti;Tomar, Shailly. And the article was included in FEBS Letters in 2020.Synthetic Route of C11H13IN4O4 The following contents are mentioned in the article:

Alphaviruses, including Chikungunya (CHIKV) and Venezuelan equine encephalitis virus (VEEV), are among the leading causes of recurrent epidemics all over the world. Alphaviral nonstructural protein 1 (nsP1) orchestrates the capping of nascent viral RNA via its S-adenosyl methionine-dependent N-7-methyltransferase (MTase) and guanylyltransferase activities. We developed and validated a novel capillary electrophoresis (CE)-based assay for measuring the MTase activity of purified VEEV and CHIKV nsP1. We employed the assay to assess the MTase inhibition efficiency of a few adenosine analogs and identified 5-iodotubercidin (5-IT) as an inhibitor of nsP1. The antiviral potency of 5-IT was evaluated in vitro using a combination of cell-based assays, which suggest that 5-IT is efficacious against CHIKV in cell culture (EC₅₀: 0.409μM). This study involved multiple reactions and reactants, such as (2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (cas: 24386-93-4Synthetic Route of C11H13IN4O4).

(2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (cas: 24386-93-4) 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 (THF) is primarily used as a precursor to polymers including for surface coating, adhesives, and printing inks.Synthetic Route of C11H13IN4O4

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

Hospitalization as an outcome in ambulatory COVID-19 trials-not applicable in every setting was written by Nunez, Isaac;Valdes-Ferrer, Sergio Ivan;Soto-Mota, Adrian. And the article was included in Clinical Microbiology and Infection in 2022.Related Products of 2492423-29-5 The following contents are mentioned in the article:

A review. The COVID-19 pandemic has stressed hospitals worldwide. Thus, most randomized trials have focused on hospitalized patients, and their primary outcomes have frequently included mech. ventilation and death. It is only until recently that treatments for ambulatory patients (remdesivir, molnupiravir, and nirmatrelvir)havebeenincludedbytheInfectiousDiseasesSociety of America in their COVID-19 guidelines. The PINETREE trial evaluated the use of remdesivir in ambulatory patients with a high risk of developing severe COVID-19. Addnl.,largevariabilitywithineachtrial is possible given different sites could have different hospital capacity, hospital occupancy, and COVID-19 caseload could bedifferent according to the geog. area. While randomization may help to reduce this bias, different recruitment rates at distinct sites may still introduce variability. This study involved multiple reactions and reactants, such as ((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate (cas: 2492423-29-5Related Products of 2492423-29-5).

((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate (cas: 2492423-29-5) 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. Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.Related Products of 2492423-29-5

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

Engineered ribosyl-1-kinase enables concise synthesis of molnupiravir, an antiviral for COVID-19 was written by McIntosh, John A.;Benkovics, Tamas;Silverman, Steven M.;Huffman, Mark A.;Kong, Jongrock;Maligres, Peter E.;Itoh, Tetsuji;Yang, Hao;Verma, Deeptak;Pan, Weilan;Ho, Hsing-I.;Vroom, Jonathan;Knight, Anders M.;Hurtak, Jessica A.;Klapars, Artis;Fryszkowska, Anna;Morris, William J.;Strotman, Neil A.;Murphy, Grant S.;Maloney, Kevin M.;Fier, Patrick S.. And the article was included in ACS Central Science in 2021.Name: ((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate The following contents are mentioned in the article:

Molnupiravir (MK-4482) is an investigational antiviral agent that is under development for the treatment of COVID-19. Given the potential high demand and urgency for this compound, it was critical to develop a short and sustainable synthesis from simple raw materials that would minimize the time needed to manufacture and supply molnupiravir. The route reported here is enabled through the invention of a novel biocatalytic cascade featuring an engineered ribosyl-1-kinase and uridine phosphorylase. These engineered enzymes were deployed with a pyruvate-oxidase-enabled phosphate recycling strategy. Compared to the initial route, this synthesis of molnupiravir is 70% shorter and approx. 7-fold higher yielding. Looking forward, the biocatalytic approach to molnupiravir outlined here is anticipated to have broad applications for streamlining the synthesis of nucleosides in general. This study involved multiple reactions and reactants, such as ((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate (cas: 2492423-29-5Name: ((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate).

((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate (cas: 2492423-29-5) 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. THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.Name: ((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate

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

Structure-activity relationship study of beta-carboline derivatives as haspin kinase inhibitors was written by Cuny, Gregory D.;Ulyanova, Natalia P.;Patnaik, Debasis;Liu, Ji-Feng;Lin, Xiangjie;Auerbach, Ken;Ray, Soumya S.;Xian, Jun;Glicksman, Marcie A.;Stein, Ross L.;Higgins, Jonathan M. G.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Safety of (2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol The following contents are mentioned in the article:

Haspin is a serine/threonine kinase that phosphorylates Thr-3 of histone H3 in mitosis that has emerged as a possible cancer therapeutic target. High throughput screening of approx. 140,000 compounds identified the β-carbolines harmine and harmol as moderately potent haspin kinase inhibitors. Based on information obtained from a structure-activity relationship study previously conducted for an acridine series of haspin inhibitors in conjunction with in silico docking using a recently disclosed crystal structure of the kinase, harmine analogs were designed that resulted in significantly increased haspin kinase inhibitory potency. The harmine derivatives also demonstrated less activity towards DYRK2 compared to the acridine series. In vitro mouse liver microsome stability and kinase profiling of a representative member of the harmine series (42, LDN-211898) are also presented. This study involved multiple reactions and reactants, such as (2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (cas: 24386-93-4Safety of (2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol).

(2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (cas: 24386-93-4) 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. 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.Safety of (2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

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

Slowly on, Slowly off: Bisubstrate-Analogue Conjugates of 5-Iodotubercidin and Histone H3 Peptide Targeting Protein Kinase Haspin was written by Kestav, Katrin;Viht, Kaido;Konovalov, Anton;Enkvist, Erki;Uri, Asko;Lavogina, Darja. And the article was included in ChemBioChem in 2017.Electric Literature of C11H13IN4O4 The following contents are mentioned in the article:

The atypical protein kinase haspin is a key player in mitosis by catalyzing the phosphorylation of Thr3 in histone H3, and thus ensuring the normal function of the chromosomal passenger complex. Here, we report the development of bisubstrate-analog inhibitors targeting haspin. The compounds were constructed by linking 5-iodotubercidin to the N terminus of histone H3 peptide. The new conjugates show high affinity (sub-nanomolar K_D) towards haspin as well as slow kinetics of association and dissociation (residence time of several hours). This reflects a unique binding mode and translated into improved selectivity. The latter was confirmed in a biochem. binding/displacement assay with a panel of ten protein kinases, in a thermal shift assay with off-targets of 5-iodotubercidin (adenosine kinase and the Cdc2-like kinase family) and in assay with spiked HeLa cell lysate. This study involved multiple reactions and reactants, such as (2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (cas: 24386-93-4Electric Literature of C11H13IN4O4).

(2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (cas: 24386-93-4) 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.Electric Literature of C11H13IN4O4

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

LC and LC-HRMS studies on stability behavior of molnupiravir an anti-COVID 19 drug was written by Jain, Sonali;Giri, Shivraj;Sharma, Nitish;Shah, Ravi P.. And the article was included in Journal of Liquid Chromatography & Related Technologies.Name: ((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate The following contents are mentioned in the article:

Molnupiravir is a recently approved drug against the ongoing worldwide pandemic of COVID-19. The current study endeavors to identify and characterize the degradation products of molnupiravir using LC-MS/MS for rapid drug development. The HPLC separation was achieved using Waters Xselect HSS T3 (75 x 4.6 mm, 2.5 μm) column with ammonium formate and ACN as mobile phase in gradient elution mode. The injection volume was 5 μL with 0.7 mL/min flow rate. The detection wavelength was 272 nm and all the study was performed at a constant column temperature of 25 °C. MS/MS study of molnupiravir and its DPs was performed at optimized mass parameters and in total four DPs were identified and characterized. The mechanistic pathway of formation of all DPs from molnupiravir is established. Online web server Pro Tox II was used to predict the in-silico safety profile of DPs in comparison to the drug. This study involved multiple reactions and reactants, such as ((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate (cas: 2492423-29-5Name: ((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate).

((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate (cas: 2492423-29-5) 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). 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.Name: ((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate

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

Bioorthogonally Functionalized NAD⁺ Analogues for In-Cell Visualization of Poly(ADP-Ribose) Formation was written by Wallrodt, Sarah;Buntz, Annette;Wang, Yan;Zumbusch, Andreas;Marx, Andreas. And the article was included in Angewandte Chemie, International Edition in 2016.Application of 24386-93-4 The following contents are mentioned in the article:

Poly(ADP-ribos)ylation (PARylation) is a major posttranslational modification and signaling event in most eukaryotes. Fundamental processes like DNA repair and transcription are coordinated by this transient polymer and its binding to proteins. ADP-ribosyltransferases (ARTs) build complex ADP-ribose chains from NAD⁺ onto various acceptor proteins. Mol. studies of PARylation thus remain challenging. Herein, we present the development of bioorthogonally functionalized NAD⁺ analogs for the imaging of PARylation in vitro and in cells. Our results show that 2-modified NAD⁺ analogs perform remarkably well and can be applied to the in-cell visualization of PARylation simultaneously in two colors. This tool gives insight into the substrate scope of ARTs and will help to further elucidate the biol. role of PARylation by offering fast optical, multichannel read-outs. This study involved multiple reactions and reactants, such as (2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (cas: 24386-93-4Application of 24386-93-4).

(2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (cas: 24386-93-4) 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 24386-93-4

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

7-Functionalized 7-deazapurine β-D and β-L-ribonucleosides related to tubercidin and 7-deazainosine: glycosylation of pyrrolo[2,3-d]pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D or β-L-ribofuranose was written by Seela, Frank;Ming, Xin. And the article was included in Tetrahedron in 2007.Computed Properties of C11H13IN4O4 The following contents are mentioned in the article:

Several 7-functionalized 7-deazapurine ribonucleosides, e.g. I, were prepared Glycosylation of 7-halogenated 6-chloro-7-deazapurines with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose or 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose gave the protected β-D-nucleosides (53-62%) and the β-L-nucleosides (57-72%), which were transformed to 7-halogenated 7-deazapurine ribonucleosides related to tubercidin and 7-deazainosine. 7-Alkynyl nucleosides were obtained from the 7-iodo nucleosides 1e and 2e employing the palladium-catalyzed Sonogashira cross-coupling reaction. Within the series of 7-deazaadenosine (tubercidin) analogs and 7-deazainosine derivatives phys. data such as pK_a values, chromatog. mobilities, ¹³C NMR chem. shifts were determined and correlated to each other. This study involved multiple reactions and reactants, such as (2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (cas: 24386-93-4Computed Properties of C11H13IN4O4).

(2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (cas: 24386-93-4) 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 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 C11H13IN4O4

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

A CoMSIA study on the adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues was written by Caballero, Julio;Fernandez, Michael;Gonzalez-Nilo, Fernando D.. And the article was included in Bioorganic & Medicinal Chemistry in 2008.SDS of cas: 24386-93-4 The following contents are mentioned in the article:

The structural requirements of pyrrolo[2,3-d]pyrimidine nucleoside (PPN) analogs as adenosine kinase (AK) inhibitors were in silico studied by using CoMSIA method. All models were trained with 32 compounds, after which they were evaluated for predictive ability with addnl. 5 compounds Quant. information on structure-activity trends is provided for further rational development and direction of selective synthesis. The best CoMSIA model included hydrophobic, H-bond donor and H-bond acceptor fields and had a good predictive quality according to internal validation criteria. In addition, this model predicted adequately the compounds contained in the test set. The anal. of the model gives a comprehensive qual. and quant. description of the mol. features at C4 and C5 positions of the pyrrolo[2,3-d]pyrimidine scaffold and C5-position of the β–ribofuranose of PPN analogs, relevant for a high AK inhibitory activity. This study involved multiple reactions and reactants, such as (2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (cas: 24386-93-4SDS of cas: 24386-93-4).

(2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (cas: 24386-93-4) 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. 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: 24386-93-4

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

Sotrovimab for Treatment of COVID-19 in Solid Organ Transplant Recipients was written by Dhand, Abhay;Okumura, Kenji;Wolfe, Kevin;Lobo, Stephen A.;Nog, Rajat;Keller, Marina;Bodin, Roxana;Singh, Nandita;Levine, Avi;Nabors, Christopher. And the article was included in Transplantation in 2022.Related Products of 2492423-29-5 The following contents are mentioned in the article:

Solid organ transplant recipients (SOTRs) may be at higher risk of developing severe coronavirus disease 2019 (COVID-19). Early use of anti-severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) monoclonal antibody in SOTRs provides a safe outpatient treatment option to reduce COVID-1 9-related risk of hospitalization and death. Sotrovimab is a recombinant human Ig-Gl-kappa monoclonal antibody that binds to a conserved epitope on the spike protein receptor-binding domain of SARS-CoV and SARS-CoV-2. Oral antiviral use is limited in SOTRs because of significant drug-drug interaction with nirmatrelvir/ritonavir and observed reduced efficacy of molnupiravir. Therefore, sotrovimab, based on its longer half-life and neutralizing activity against almost all the currently known coronavirus variants, potentially offers another safe and efficacious therapy for outpatient management of SOTRs with mild to moderate COVID-19. This study involved multiple reactions and reactants, such as ((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate (cas: 2492423-29-5Related Products of 2492423-29-5).

((2R,3S,4R,5R)-3,4-Dihydroxy-5-((Z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate (cas: 2492423-29-5) 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.Related Products of 2492423-29-5

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