Category: Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

To a mixture of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate(20 g, 116 mmol) in anhydrous THF (300 mE) was addedlithium aluminum hydride (8.8 g, 232 mmol) portionwise at0 C. The mixture was stirred at 11-13 C. for 18 h. TEC(petroleum ether: ethyl acetate=3: 1) showed no startingmaterial remaining. The mixture was quenched with water(9 mE), 10% aq. NaOH solution (9 mE) and water (18 mE)successively at 0 C., filtered and concentrated underreduced pressure to give crude 2-(tetrahydro-2H-pyran-4-yl)ethanol (11.7 g, 77%) as an oil, which was used for thenext step directly without further purification. ?H NMR(CDC13, 400 MHz): oe 3.86-3.90 (m, 2H), 3.58-3.61 (t, J=6.4Hz, 2H), 3.32-3.35 (t, J=11.6 Hz, 2H), 2.69-2.70 (m, 1H),1.61-1.63 (m, 3H), 1.54-1.60 (m, 2H), 1.43-1.45 (m, 2H).

As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

Reference£º
Patent; Vitae Pharmaceuticals, Inc.; Claremon, David A.; Yuan, Jing; Zhao, Wei; Zheng, Yajun; (54 pag.)US9481674; (2016); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.40191-32-0,Tetrahydro-2H-pyran-4-carbonyl chloride,as a common compound, the synthetic route is as follows.

The (S)-pyrrolidin-3-ol hydrochloride (3.69g, 29.9 mmol) and triethylamine (6.65 g, 9.16 mL, 65.7 mmol) were put in CH2CI2(15 mL). The suspension was cooled at ~3C. To this mixture, a solution of tetrahydro-pyran-4-carbonyl chloride (4.67g, 29.9 mmol) in CH2CI2(15 mL) was added slowly. Then the resulting reaction mixture was stirred for 1 .5h at 3-10C. The reaction mixture was then concentrated to give a powder. To this powder, addition of EtOAc (100 mL). The solid was filtered and washed with EtOAc. The recovered filtrate was then concentrated to give ((S)-3-hydroxy-pyrrolidin-1 -yl)-(tetrahydro-pyran-4-yl)-methanone as beige powder. (6.77 g, 98% yield).1H-NMR (400 MHz, Methanol-d4 298 K): delta ppm 1 .59-2.15 (m, 6H) 2.69-2.86 (m, 1 H) 3.43-3.75 (m, 6H) 3.94-4.00 (m, 2H) 4.37-4.48 (m, 1 H). LCMS: [M+H]+= 199.9, Rt(6)= 0.86 min

As the paragraph descriping shows that 40191-32-0 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3301-94-8,6-Butyltetrahydro-2H-pyran-2-one,as a common compound, the synthetic route is as follows.

General procedure: The lactonase, phosphotriesterase, and esterase hydrolyses of GkaP were monitored by absorbance changes in a UV-2550 spectrophotometer (Shimadzu, Kyoto, Japan) at a constant temperature of 75C with 1 mL reaction volumes (path length = 1cm). Analysis of reaction samples for each substrate was performed at a constant enzyme concentration. The delta-decanolactone substrate was dissolved in dimethyl sulfoxide (DMSO), whereas the p-nitrophenylcaprylate and OP substrates in acetonitrile as stock solutions. For enzymatic kinetics assay, aliquots of the stock were added to the reaction buffer for defined concentrations. The hydrolysis of lactone was monitored using a pH-sensitive colorimetric assay [33]. Briefly, the reactions were performed in 2.5 mM Bicine (pH 8.3) containing 0.2MNaCl, 0.2 mM cresol purple, and 0.02-20 mM lactone substrate. Upon mixture of the substrate with the enzyme, the decrease inabsorbance was monitored at 577 nm (epsilon577 = 47300 M-1cm-1, 1%DMSO). The enzyme was diafiltrated with 10 mM bicine (pH 8.3), with a PD-10 column (GE Healthcare, Shanghai, China) before use. Kinetic measurements with p-nitrophenyl caprylate (pNPC8), and ethyl-paraoxon were performed in 50 mM phosphate buffer (pH 8.0). The reaction rates were monitored bythe release of p-nitrophenol (epsilon405 = 16000M-1cm-1, 2% acetonitrile). The initial rates were corrected for the background rate of spontaneous hydrolysis in the absence of enzymes, which were subtracted from the enzymatic rates. The kinetic parameters (kcat, Km) were obtained byfitting the data to the Michaelis-Menten equation [V = S¡ÁE¡Ákcat/(S+Km)] or to the pseudo first-order form of it at S<Article; Zhang, Yu; An, Jiao; Yang, Guang-Yu; Bai, Aixi; Zheng, Baisong; Lou, Zhiyong; Wu, Geng; Ye, Wei; Chen, Hai-Feng; Feng, Yan; Manco, Giuseppe; PLoS ONE; vol. 10; 2; (2015);,
Tetrahydropyran – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.127956-11-0,Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of methyl 4-oxotetrahydro-2H-pyran-3-carboxylate (51.1 g, 323 mmol) and benzyl 2-amino-2-iminoethylcarbamate hydrochloride (78.8 g, 323 mmol) in anhydrous ethanol was added sodium ethoxide (122 mL, 323 mmol, 21 % in ethanol). The mixture was mechanically stirred, heated at reflux for 24 h, cooled down to ambient temperature, and filtered to give the title compound (55.6 g, 55% yield). 1 H NMR (400 MHz, DMSO- d6) delta 12.40 (br. s., 1 H), 7.69 (t, J=5.8 Hz, 1 H), 7.15 – 7.44 (m, 5 H), 4.99 – 5.08 (m, 2 H), 4.35 (s, 2 H), 4.04 – 4.1 1 (m, 2 H), 3.84 (t, J=5.3 Hz, 2 H), 2.48 – 2.57 (m, 2 H). MS m/z 316.2 (M+1 ), retention time = 1.10 min.

As the paragraph descriping shows that 127956-11-0 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; CHEUNG, Atwood, Kim; CHIN, Donoval, Noel; FAN, Jianmei; SHULTZ, Michael, David; TOMLINSON, Ronald, Charles; WO2013/10092; (2013); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 14: Preparation of GRV5-methyl-3-f2-oxo-2(r(lR)-l-rhohenylethvnamino>ethvD hexanoic acid compound (24); [0088] A three-necked flask equipped with an addition funnel, thermometer pocket, drying tube and a mechanical stirrer, was charged with ethanol (100 ml), (R)-(+)- phenylethylamine (35.58 g, 0.147mole) and 4-dimethylaminopyridine (0.18 g, 0.00147 mole). The mixture was cooled to a temperature of 0-5 C, followed by addition of a solution of 3-isobutyl glutaric anhydride (25 g, 0.147 mole) in ethanol (25 ml), over a period of 15-20 minutes, and stirring for additional 1.5-2 hours, at a temperature of 0-50C. The solvent was stripped off and the residue was extracted with 2.5-3 percent aqueous solution of NaOH solution (500 ml), and diluted with water (1000 ml) followed by washing the aqueous phase with toluene (1 x 100 ml and 1 x 50 ml). The pH of the aqueous phase was adjusted to 2-2.5 by adding a 1-12N solution of hydrochloric acid. The aqueous phase was further extracted with ethyl acetate (1 x 150 ml and 1 x 50 ml), followed by drying the combined ethyl acetates extracts over anhydrous sodium sulfate, and stripping off the solvents, to obtain a residue. The residue was crystallized from ethyl acetate and toluene mixture to get 22.7 g (53.09 percent yield) of a white solid of (3R)-5-methyl-3-(2-oxo-2-{[(lR)-l- phenylethyl] amino }ethyl)hexanoic acid with an optical purity of 99.17 percent, as measured by chiral HPLC.

The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2007/35789; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

85064-61-5, Tetrahydropyranyl-4-acetic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Triethylamine (14.84 mmol) was added to a solution of the carboxylic acid (7.42 mmol) in THF (31.0 mL, 0.2 M) at room temperature, stirred for 10 min, and then cooled to 0 C before addition of pivaloyl chloride (8.90 mmol). After 30 min at 0 C, lithium chloride (0.5 M in THF, 8.90 mmol) was added, followed by (R)-(+)- or (S)-(-)-4-benzyloxazolidin-2-one (8.90 mmol) and the mixture was stirred at room temperature for 20 h. The mixture was partitioned with EtOAc (20 mL) and 1M HCl (3*20 mL) and the organic layer was washed with 1M K2CO3 (3*20mL). The acidic aqueous layer was extracted with EtOAc (20 mL) and the combined organic layer was washed with brine (10 mL), dried (MgSO4), filtered, and concentrated under vacuum. The crude material was purified as indicated.

The synthetic route of 85064-61-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Shouksmith, Andrew E.; Evans, Laura E.; Tweddle, Deborah A.; Miller, Duncan C.; Willmore, Elaine; Newell, David R.; Golding, Bernard T.; Griffin, Roger J.; Australian Journal of Chemistry; vol. 68; 4; (2015); p. 660 – 679;,
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Tetrahydropyran – an overview | ScienceDirect Topics

1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 1G 4-{4-[(4′-chloro-1,1′-biphenyl-2-yl)methyl]piperazin-1-yl}-N-({3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}sulfonyl)-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide EXAMPLE 1E (115 mg), EXAMPLE 1F (67 mg), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (82 mg), and 4-dimethylaminopyridine (26 mg) were stirred in CH2Cl2 (3 mL) for 24 hours. The reaction was cooled and chromatographed on silica gel with 0-5% methanol/ethyl acetate. 1H NMR (300 MHz, dimethylsulfoxide-d6) delta 11.48 (brs, 1H), 8.34 (br s, 1H), 8.31 (m, 1H), 7.90 (d, 1H), 7.68 (m, 1H), 7.58 (m, 2H), 7.46 (m, 4H), 7.35 (m, 2H), 7.21 (dd, 1H), 6.76 (m, 4H), 6.28 (m, 2H), 3.02 (m, 2H), 2.89 (m, 4H), 2.80 (m, 4H), 2.40 (m, 3H), 1.59 (m, 2H), 1.25 (m, 4H), 0.87 (m, 2H).

The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBOTT LABORATORIES; US2010/305122; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

Lithium aluminum hydride (2M solution in THF, 40.66 ml, 81.3 mmol) was cooled at 0 C and a solution of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (14.0 g, 81.3 mmol) in THF (70 ml) was added dropwise. Ethyl acetate (20 ml) was added to the reaction mixture dropwise at 0 C and the resulting mixture was allowed to stir for 16 h. The reaction mixture was filtered through Celite and the filtrate was concentrated to give crude compound. The crude material was purified by column chromatography using mobile phase 0-65% ethyl acetate in hexane to afford the title compound (66.1%). ?H NMR (400MHz, CDC13) & 5.71 (s, 1H), 4.18-4.15 (m, 2H), 3.81-3.75 (m, 4H), 3.05-3.02 (m, 2H), 2.37-2.34 (m, 2H), 1.32- 1.31 (m, 3H).

The synthetic route of 103260-44-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EPIZYME, INC.; CHESWORTH, Richard; MITCHELL, Lorna, Helen; CAMPBELL, John, Emmerson; REITER, Lawrence, Alan; SWINGER, Kerren, Kalai; (387 pag.)WO2016/44626; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.36838-71-8,4-Methylenetetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A mixture of 4-methylene-tetrahydropyran (50 mg) and 9-bora-bicyclo{3.3.1}nonane (0.5 M solution in tetrahydrofuran, 1 mL) is stirred for 6 h at room temperature. The solution is used directly for the next step.

The synthetic route of 36838-71-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; LANGKOPF, Elke; WAGNER, Holger; WO2014/86712; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

To a solution of tetrahydro-2H-pyran-4-ol (10.0 g) in DCM (200 mL)was added TEA (12.9 g) and methanesulfonyl chloride (11.3 g). The mixture was stirred at 0C for 1 hour, and then washed with H20. The organic layer was dried over Na2SO4 and concentrated to afford10 tetrahydro-2H-pyran-4-yl methanesulfonate (15.5 g).

2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHEN, Weichun; IGBOKO, Ebere F; LIN, Xichen; LU, Hongfu; REN, Feng; WREN, Paul Bryan; XU, Zhongmiao; YANG, Ting; ZHU, Lingdong; WO2015/181186; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics