Category: Tetrahydrofurans

One-pot bi-enzymatic cascade synthesis of puerarin polyfructosides was written by Nunez-Lopez, Gema;Morel, Sandrine;Hernandez, Lazaro;Musacchio, Alexis;Amaya-Delgado, Lorena;Gschaedler, Anne;Remaud-Simeon, Magali;Arrizon, Javier. And the article was included in Carbohydrate Polymers in 2020.SDS of cas: 470-69-9 This article mentions the following:

Enzymic glycosylation is an efficient way to increase the water solubility and the bioavailability of flavonoids. Levansucrases from Bacillus subtilis (Bs_SacB), Gluconacetobacter diazotrophicus (Gd_LsdA), Leuconostoc mesenteroides (Lm_LevS) and Zymomonas mobilis (Zm_LevU) were screened for puerarin (daidzein-8-C-glucoside) fructosylation. Gd_LsdA transferred the fructosyl unit of sucrose onto the glucosyl unit of the acceptor forming β-D-fructofuranosyl-(2→6)-puerarin (P1a), while Bs_SacB, Lm_LevS and Zm_LevU synthesized puerarin-4′-O-β-D-fructofuranoside (P1b) and traces of P1a. The Gd_LsdA product P1a was purified and assayed as precursor for the synthesis of puerarin polyfructosides (PPFs). Bs_SacB elongated P1a more competently forming a linear series of water-soluble PPFs reaching at least 21 fructosyl units, as characterized by HPLC-UV-MS, HPSEC and MALDI-TOF-MS. Simultaneous or sequential Gd_LsdA/Bs_SacB reactions yielded PPFs directly from puerarin with the acceptor conversion ranging 82-92 %. The bi-enzymic cascade synthesis of PPFs in the same reactor avoided the isolation of the intermediate product P1a and it is appropriate for use at industrial scale. 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: 470-69-9SDS of cas: 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.SDS of cas: 470-69-9

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

Click reactivity of azide-modified polyvinyl chloride as an entry to glycopolymer scaffolds was written by Ay, Emriye;Yenil, Nilgun. And the article was included in Croatica Chemica Acta in 2021.SDS of cas: 582-52-5 This article mentions the following:

We report the synthesis of new carbohydrate/triazole polymers based on poly(viny chloride) (PVC). Azide incorporation into com. available PVC was carried out using nucleophilic substitution and Cu-catalyzed reaction of the resulting PVC-N₃ using three alkynyl-containing acetonide-protected monosaccharides (based on D-glucose and D-galactose) provided a set of PVC-based polymers incorporating a triazolyl linkage with monosaccharide moieties present on the periphery. Modified polymers were characterized by using Fourier transform IR (FT-IR), NMR (¹H-NMR and ¹³C-NMR) spectroscopy, together with thermogravimetric and surface morphol. anal. 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

Site-selective palladium-catalyzed 1,1-arylamination of terminal alkenes was written by Han, Chunhua;Cai, Libo;Zhang, Dongquan;Pan, Rui;Li, Qiuyu;Lin, Aijun;Yao, Hequan. And the article was included in CCS Chemistry in 2022.Electric Literature of C12H20O6 This article mentions the following:

Many of the commonly used pharmaceuticals and biol. active natural products are nitrogen-containing compounds Recently, the transition-metal-catalyzed or the radical-mediated 1,2-carboamination of alkenes has been well explored to access amine scaffolds. However, synthetic strategies toward the 1,1-carboamination of alkenes are severely limited. Herein, we describe a method to achieve the 1,1-arylamination using readily available building blocks enabled by palladium catalysis. This sequential three step-Heck arylation, metal migration, followed by aza-1,6-Micheal addition process exhibits excellent chemo- and regioselectivity. To showcase the potential as a method for diversity-oriented drug discovery, the modification of numerous structurally complex bioactive mols. was also successfully performed. 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: 582-52-5Electric Literature 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 water-miscible and has a low viscosity making it a highly versatile solvent used in a variety of industries. Commercial tetrahydrofuran contains substantial water that must be removed for sensitive operations, e.g. those involving organometallic compounds. Although tetrahydrofuran is traditionally dried by distillation from an aggressive desiccant, molecular sieves are superior.Electric Literature of C12H20O6

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

Study of synthesis of sucrose octaacetate was written by Liu, Yuanfeng;Wumanjiang, E-Li;Wen, Bin. And the article was included in Riyong Huaxue Gongye in 2002.Category: tetrahydrofurans This article mentions the following:

Sucrose octaacetate, a nonionic surfactant, was prepared by esterification with Ac₂O using several alkali metal salt catalysts. The effect of reaction conditions on product yield was studied. Under optimum conditions, the product yield reached 93.8%. 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: 126-14-7Category: tetrahydrofurans).

(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. 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.Category: tetrahydrofurans

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

Prediction the contents of fructose, glucose, sucrose, fructooligosaccharides and iridoid glycosides in Morinda officinalis radix using near-infrared spectroscopy was written by Hao, Qingxiu;Zhou, Jie;Zhou, Li;Kang, Liping;Nan, Tiegui;Yu, Yi;Guo, Lanping. And the article was included in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy in 2020.Related Products of 470-69-9 This article mentions the following:

Morindae officinalis radix (MOR) is a famous Chinese herbal medicine which has long history of use in medicine and food. MOR and MOR with steaming process (PMOR) are the most commonly used forms in clin. and health care. In order to establish a fast and mostly nondestructive quality control method for MOR, 183 beaches of MOR samples and 20 beaches of PMOR samples were collected com. from major producing areas in Guangdong, Fujian and Guangxi Provinces of China. To predict main components of MOR, a calibration model was established based on near-IR spectroscopy with partial least square regression. The model was optimized by compared the parameters of root mean square error of prediction (RMSEP), root mean square error of cross validation (RMSECV), coefficient of correlation (R²) and ratio of performance to deviation (RPD). Comparative studies were performed to evaluate the performance of models by different spectra preprocessing methods and different data set. The results showed that the model performance was improved with standard normal variate spectra preprocessing methods and when the data set contained both MOR and PMOR samples. A few PMOR samples were added to MOR samples data set the model predictive performance could be improved. The contents of 14 components were predicted in MOR with lower RMSEP and RMSECV, and higher R² and RPD, including fructose (12.8 mg/g, 16.3 mg/g, 0.9873, 10.10), glucose (7.28 mg/g, 8.73 mg/g, 0.9611, 6.21) sucrose (9.24 mg/g, 9.10 mg/g, 0.8419, 1.75), GF2(9.42 mg/g, 11.3 mg/g, 0.8526, 2.03), GF3(7.98 mg/g, 9.20 mg/g, 0.8756, 2.74), GF4(6.81 mg/g, 8.93 mg/g, 0.8663, 3.06), GF5(8.13 mg/g, 8.85 mg/g, 0.9001, 3.06), GF6(6.40 mg/g, 6.95 mg/g, 0.9145, 3.27), GF7(5.53 mg/g, 6.15 mg/g, 0.9195, 3.57), GF8(5.40 mg/g, 6.02 mg/g, 0.9179, 3.31), GF9(3.00 mg/g,4.35 mg/g,0.9446, 5.03),GF10(4.08 mg/g, 5.34 mg/g, 0.8983, 3.62), GF11(8.97 mg/g, 7.70 mg/g, 0.8683, 2.01) and iridoid glycosides (4.12 mg/g, 5.51 mg/g, 0.8712, 2.43). The model established in this paper could predict 14 components of MOR. The results would provide a reference method for the quality control of Chinese medical materials and their process products. 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: 470-69-9Related Products 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. 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.Related Products of 470-69-9

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

Feasibility of deuterium magnetic resonance spectroscopy of 3-O-Methylglucose at 7 Tesla was written by Hartmann, Benedikt;Mueller, Max;Seyler, Lisa;Baeuerle, Tobias;Wilferth, Tobias;Avdievitch, Nikolai;Ruhm, Loreen;Henning, Anke;Lesiv, Alexei;Ivashkin, Pavel;Uder, Michael;Nagel, Armin M.. And the article was included in PLoS One in 2021.COA of Formula: C12H20O6 This article mentions the following:

Deuterium Magnetic Resonance Spectroscopy (DMRS) is a non-invasive technique that allows the detection of deuterated compounds in vivo. DMRS has a large potential to analyze uptake, perfusion, washout or metabolism, since deuterium is a stable isotope and therefore does not decay during biol. processing of a deuterium labeled substance. Moreover, DMRS allows the distinction between different deuterated substances. In this work, we performed DMRS of deuterated 3-O-Methylglucose (OMG). OMG is a non-metabolizable glucose analog which is transported similar to D-glucose. DMRS of OMG was performed in phantom and in vivo measurements using a preclin. 7 T MRI system. The chem. shift (3.51 ± 0.1 ppm) and relaxation times were determined OMG was injected i.v. and spectra were acquired over a period of one hour to monitor the time evolution of the deuterium signal in tumor-bearing rats. The increase and washout of OMG could be observed Three different exponential functions were compared in terms of how well they describe the OMG washout. A mono-exponential model with offset seems to describe the observed time course best with a time constant of 1910 ± 770 s and an offset of 2.5 ± 1.2 mmol/l (mean ± std, N = 3). Chem. shift imaging could be performed with a voxel size of 7.1 mm x 7.1 mm x 7.9 mm. The feasibility of DMRS with deuterium labeled OMG could be demonstrated. These data might serve as basis for future studies that aim to characterize glucose transport using DMRS. 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. Solid acid catalysis, and the advantages often associated with their use, have been proved equally efficient for the synthesis of tetrahydrofurans or furans. Commercial tetrahydrofuran contains substantial water that must be removed for sensitive operations, e.g. those involving organometallic compounds. Although tetrahydrofuran is traditionally dried by distillation from an aggressive desiccant, molecular sieves are superior.COA of Formula: C12H20O6

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

Three-Component Coupling of α-Trifluoromethyl Carbonyls, Azides and Amines for the Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles was written by Gao, Ge;Kuantao;Mao;Lv, Leiyang;Li, Zhiping. And the article was included in Advanced Synthesis & Catalysis in 2022.Reference of 582-52-5 This article mentions the following:

A metal-free three-component coupling of α-CF₃ carbonyls, azides and amines for the regioselective synthesis of 1,4,5-trisubstituted 1,2,3-triazoles has been established. Various substituted amide-functionalized 1,2,3-triazoles I (Ar = Ph, 3-O₂NC₆H₄, 3-pyridyl, etc.; R = Me, Ph, 4-BrC₆H₄, 2-naphthyl, 5-methyl-2-furyl, etc.; X = 1-pyrrolidinyl, 1-piperidinyl, etc.) were obtained when the enolizable α-CF₃ ketones RC(O)CH₂CF₃ were reacted with azides ArN₃ and amines HX in aqueous reaction medium. Control and ¹⁸O-labeling experiments revealed that the in situ generated β-oxo amide was responsible for the formal oxygen-shift and the subsequent [3+2] cycloaddition reaction, with amine as both the catalyst and reactant. In the case of non-enolizable α-CF₃ esters F₃CCH₂CO₂R¹ (R¹ = PhCH₂, 1-adamantylmethyl, etc.), the densely functionalized 5-amino 1,2,3-triazoles II were achieved exclusively, which could enable the late-stage functionalization of complex biol. mols. 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. 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.Reference of 582-52-5

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

A method for preparing N-alkylated kanosamines from diacetone D-glucose was written by Cannone, Zachary P.;Peczuh, Mark W.. And the article was included in Tetrahedron Letters in 2019.Product Details of 582-52-5 This article mentions the following:

The aminoglycoside (AG) antibiotics have seen a resurgence in their clin. use given the increase in multi drug resistant bacterial infections. Campaigns to generate novel analogs show promise that structural modification can lead to compounds with improved pharmacol. properties. The results described herein include a new method to synthesize mono-, di-, and mixed N-alkylated kanosamine sugars and their elaboration into novel glycosides that inhibit bacterial protein synthesis in vitro. 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. 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.Product Details of 582-52-5

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

Visible-light-induced photo-acid catalysis: application in glycosylation with O-glycosyl trichloroacetimidates was written by Zhao, Gaoyuan;Li, Juncheng;Wang, Ting. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.Computed Properties of C12H20O6 This article mentions the following:

The development of visible-light-induced photoacid catalyzed glycosylation is reported. The eosin Y and PhSSPh catalyst system is applied to realize glycosylation with different glycosyl donors upon light irradiation The reaction shows a broad substrate scope, including both glycosyl donors and acceptors, and highlights the mild nature of the reaction conditions. 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. 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.Computed Properties of C12H20O6

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

Bitter-induced salivary proteins increase detection threshold of quinine, but not sucrose was written by Martin, Laura E.;Kay, Kristen E.;Torregrossa, Ann-Marie. And the article was included in Chemical Senses in 2019.Product Details of 126-14-7 This article mentions the following:

Exposures to dietary tannic acid (TA, 3%) and quinine (0.375%) upregulate partially overlapping sets of salivary proteins which are concurrent with changes in taste-driven behaviors, such as rate of feeding and brief access licking to quinine. In addition, the presence of salivary proteins reduces chorda tympani responding to quinine. Together these data suggest that salivary proteins play a role in bitter taste. We hypothesized that salivary proteins altered orosensory feedback to bitter by decreasing sensitivity to the stimulus. To that end, we used diet exposure to alter salivary proteins, then assessed an animal’s ability to detect quinine, using a 2-response operant task. Rats were asked to discriminate descending concentrations of quinine from water in a modified forced-choice paradigm, before and after exposure to diets that alter salivary protein expression in a similar way (0.375% quinine or 3% TA), or 1 of 2 control diets. Control animals received either a bitter diet that does not upregulate salivary proteins (4% sucrose octaacetate), or a nonbitter diet. The rats exposed to salivary protein-inducing diets significantly decreased their performance (had higher detection thresholds) after diet exposure, whereas rats in the control conditions did not alter performance after diet exposure. A fifth group of animals were trained to detect sucrose before and after they were maintained on the 3% TA diet. There was no significant difference in performance, suggesting that these shifts in threshold are stimulus specific rather than task specific. Taken together, these results suggest that salivary proteins reduce sensitivity to quinine. 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: 126-14-7Product Details 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. 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.Product Details of 126-14-7

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