Category: 19752-84-2

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 3,4,5-tribromo-1 /-/-pyrazole (21 g, 69 mmol) in THF (200 mL) were added tetrahydro-2H-pyran-3-ol (8.5 g, 83 mmol), PPh3(36 g, 138 mmol), DIAD (27 g, 138 mmol) at 0 C. The resulting mixture was stirred at 0 C for 3 hrs. The mixture was poured into water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous Na2S04and concentrated. The crude was purified by column chromatography on silica gel (PE: EtOAc= 10: 1 ) to give the title compound as oilsolid (10 g, yield 50%)., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DING, Xiao; HO, Ming-Hsun; REN, Feng; YU, Haihua; ZHAN, Yang; (290 pag.)WO2019/12093; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1.48 g of a 57% oil dispersion of sodium hydride was washed with pentane to remove the oil and the sodium hydride was suspended in 10 ml of dimethylformamide. Under a nitrogen atmosphere at 1 C., the suspension was stirred while a solution of 3.00 g of 1A in 15 ml of dimethylformamide was added drop by drop. The mixture was allowed to warm to room temperature and held there for about 1.5 hours, then was cooled to 3-4 C., and a solution of 3.72 g of benzyl chloride in 5 ml of dimethylformamide was added. The mixture was stirred for one hour, then partially stripped of solvent, and the residue was held in a refrigerator overnight. Then most of the solvent was stripped and the residue was stirred in a mixture of equal volumes of water and methylene chloride. The two phases were separated; the aqueous phase was brought to pH 7 with 6 N hydrochloric acid, and extracted with methylene chloride. The organic phases were combined, washed with saturated sodium bicarbonate solution, then with saturated sodium chloride solution, dried (MgSO4) and stripped of solvent. The residue was distilled. 1 was obtained as the fraction boiling at 76 C., 0.1 Torr., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shell Oil Company; US4388104; (1983); A;,
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.19752-84-2,Tetrahydro-2H-pyran-3-ol,as a common compound, the synthetic route is as follows.

solution of 3,5-difluorophenol (1.15 g, 8.81 mmol), tetrahydro-2H-pyran-3-ol (0.900 g, 8.81 mmol), triphenylphosphine (2.31 g, 8.81 mmol) and DIAD (1.74 mL, 8.81 mmol) in THF (10 mL) was stirred overnight. The solution was then concentrated under reduced pressure and the residue was purified by purified by column chromatography on silica gel using CombiFlash apparatus eluting with EtOAc/hexanes (0-30%). The purification afforded 1.43 g (75.8%) of the sub-title compound as a colorless oil., 19752-84-2

As the paragraph descriping shows that 19752-84-2 is playing an increasingly important role.

Reference£º
Patent; INCYTE CORPORATION; Xue, Chu-Biao; Li, Yun-Long; Geng, Hao; Pan, Jun; Wang, Anlai; Zhang, Ke; Yao, Wenqing; Zhang, Fenglei; Zhuo, Jincong; US2014/200227; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 3-hydroxytetrahydropyran (Astatech, 2.0 g, 20 mmol) in N,N- dimethylformamide (40 mL) was stirred in an ice-water bath under an atmosphere of Argon. Sodium hydride (60 % in mineral oil, 0.79 g, 20 mmol) was added in a single portion. The mixture was stirred at 0 C for one hour and then the cooling bath was removed. To the mixture was added via syringe 5-bromo-2-fluorobenzonitrile (Matrix Scientific, 3.3 g, 17 mmol) as a solution in A/,A/-dimethylformamide (20 mL) at room temperature. Mixture was stirred for 3 hours at 50 C block and then allowed to cool to room temperature. Water was added and the resulting precipitate was collected by filtration, washed with water, dried under house vacuum and then in vacuum oven over P205 to provide the desired material. 1H NMR (400 MHz, DMSO-d6) delta 8.04 (d, J = 2.5 Hz, 1 H), 7.84 (dd, J = 9.1 , 2.6 Hz, 1 H), 7.35 (d, J = 9.1 Hz, 1 H), 4.64 (m, 1 H), 3.82 (m, 1 H), 3.63 (m, 3H), 2.05 (m, 1 H), 1.83 (m, 2H), 1.57 (m, 1 H)., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GILEAD SCIENCES, INC.; DU, Zhimin; GUERRERO, Juan, Arnaldo; KAPLAN, Joshua, Aaron; KNOX, JR., John Edward; NADUTHAMBI, Devan; PHILLIPS, Barton, W.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William, J.; ZABLOCKI, Jeff; WO2015/187684; (2015); 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.19752-84-2,Tetrahydro-2H-pyran-3-ol,as a common compound, the synthetic route is as follows.

EXAMPLE IDSTEP 2: Displacement of the leaving group with 6 membered 3- hydroxyheteroalkoxyalkyl compounds for the synthesis of 42-0-(heteroaIkoxyaIkyl) rapamycin compound.Preparation of 42-0-(tetrahydropyran-3-yl), rapamycin (Merilimus 3)A reaction flask containing triflate intermediate of step-1 was further cooled to -50 C temperature and 6.07 grams (46mmol) of N,N-di-n-butylethylamine (DNBEA) followed by 1.17 grams (13.8mmol) of tetrahydropyran-3-ol compound in methylene chloride were added. The reaction mixture was stirred at -10 C temperature for 12 hours. The reaction mixture was then allowed to warm to 15 C temperature and continuously stirred for 48 hours.The reaction mixture was further concentrated by evaporation under reduced pressure to provide a pale yellow viscous mass. The quantitative HPLC of reaction mass shows theoretical yield of 62%. This mass was purified by preparative HPLC (MeOH (65%): ACN (15%): H20 (20%)) to obtain the desired product in about 65% purity. Further purification was done by combiflash (0-40% EtOAc in Hexane) to get 42-0- (tetrahydropyran-3-yl) rapamycin compound having 97.3% purity by HPLC. Then stabilizing agent BHT in acetone was homogeneously mixed with purified compound and isolation & drying steps were carried out to get white solid powder of 42-0- (tetrahydropyran-3-yl) rapamycin compound. C56H87N014 Mol. Wt.: 998.2742-0-(tetrahydropyran-3-yl), rapamycin REACTION SCHEME-DThe 42-0-(tetrahydropyran-3-yl) rapamycin compound thus obtained was analytically identified., 19752-84-2

Big data shows that 19752-84-2 is playing an increasingly important role.

Reference£º
Patent; MERIL LIFE SCIENCES PVT. LTD; RANE, Dhananjay, Sharad; VYAS, Rajnikant, Gandalal; MINOCHA, Pramod, Kumar; WO2012/17449; (2012); 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.19752-84-2,Tetrahydro-2H-pyran-3-ol,as a common compound, the synthetic route is as follows.

To a stirring solution of carbonyl carbonyldiimidazole (0.15 g, 0.93) in THF (4 mL) under an atmosphere of nitrogen was added 2-tetrahydropyran-4-ol (0.09 g, 0.93 mmol) at 5C. The resulting mix was stirred at room temperature for one hour and then added to a stirring mix of [4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine hydrochloride (0.26 g, 0.93 mmol) and DBU in tetrahydrofuran (2 mL). The reaction mixture was allowed to react for 18 hours at room temperature then poured onto water and extracted with ethyl acetate. The combined organic layers were, dried over sodium sulfate, and filtered. The solvent was removed under reduced pressure and the resultant crude residue was purified by reverse phase high pressure liquid chromatography to afford 0.13 g of the titled compound as a yellow oil. LC/MS (Method A) retention time = 1.01 minutes, minutes, 372 (M+H). 1NMR (400 MHz, CDCIs) delta ppm: 8.1 1 (d, 2H), 7.45 (d, 2H), 5.10 (sbr, 2H), 4.89 (m, 2H), 4.47 (d,2H), 3.92 (m, 2H), 3.34 (m, 2H), 1.97 (m, 2H), 1 .69 (m, 2H). 19F NMR (400 MHz, CDCI3) delta ppm: -65.34 (s)., 19752-84-2

As the paragraph descriping shows that 19752-84-2 is playing an increasingly important role.

Reference£º
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; BEAUDEGNIES, Renaud; POULIOT, Martin; (88 pag.)WO2017/103223; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 3-hydroxytetrahydropyrane (1 .8 mL, 19.58 mmol) in toluene (30 mL), under nitrogen, was added triphenylphosphine (7.7 g, 29.37 mmol) and di-tertbutylazodicarboxylate (5.4 g, 23.50 mmol). The reaction mixture was stirred at RT for 60 h. The reaction mixture was concentrated then suspended in MeOH (55 mL), followed by addition of a hydrogen chloride solution (4 M in dioxane, 39.17 mL, 156.7 mmol). The reaction mixture was stirred at RT for 16 h, filtered, and the filtrate was concentrated under reduced pressure. EtOAc was then added to the resulting residue followed by filtration. The solid collected was washed with EtOAc to afford titled compound (2.99 g, 19.58 mmol, assumed quantitative yield) as a yellow solid.1H NMR (400 MHz, DMSO-d6, ): 3.91-3.82 (m, 1H), 3.76-3.58 (m, 1H), 3.45-3.29 (m,2H), 3.04-2.94 (m, 1 H), 2.00-1.90 (m, 1 H), 1.77-1.65 (m, 1 H), 1.62-1.37 (m, 2H)., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (266 pag.)WO2017/103611; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of Intermediate 227A (32.6 mg, 0.06 mmol) in THF (1 mL) was added tetrahydro-2H-pyran-3-ol (61.3 mg, 0.600 mmol) and KHDMS (0.120 mL, 1M,0.120 mmol). The mixture was stirred at room temperature for 1 hour. TLC and LCMS indicated completion of the reaction. The reaction was quenched with iN HC1, extracted with EtOAc, the combined organic layer was washed with saturated sodium bicarbonate, brine, dried over sodium sulfate and concentrated. The compound was dissolved in DMSO and purified via preparative LC/MS (Method D: Gradient: 45-90% B over 20minutes, then a 5-minute hold at 100% B). Fractions containing the desired product were combined and dried via centrifugal evaporation to Example 234 (1.6 mg, 3.00 imol, 5.00 % yield). ?H NMR (500MHz, DMSO-d6) 8.67 (s, 1H), 8.52 (s, 1H), 7.86 (d, J8.9 Hz, 1H), 7.77 (s, 1H), 7.72-7.42 (m, 2H), 7.02 (d, J=8.8 Hz, 1H), 5.02 (br. s., 1H), 4.49 (br. s., 1H), 4.04 (s, 3H), 3.53-3.41 (m, 3H), 3.34 (br. s., 2H), 3.18-3.09 (m, 1H), 2.59 (s,3H), 1.83 (br. s., 1H), 1.66 (br. s., 1H), 1.57 (br. s., 1H), 1.42 (br. s., 1H). LC-MS:method L, RT = 2.32 mm, MS (ESI) m/z: 507.30 (M+H)t Analytical HPLC purity (method B): 95%., 19752-84-2

As the paragraph descriping shows that 19752-84-2 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; HALPERN, Oz Scott; JIANG, Wen; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (545 pag.)WO2018/13776; (2018); 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.19752-84-2,Tetrahydro-2H-pyran-3-ol,as a common compound, the synthetic route is as follows.

Combine tetrahydropyran-3-ol (1.3 g. 13 mmoi), 1-(methyisuifoni)-3-nitro-1H- pyrazole (2.4 g, 1.0 eq), and cesium carbonate (4.8 g, 1.2 eq) in acetonitrile (40 mL). Stir at 90 ?C overnight. Concentrate the mixture in vacuo. Dilute with EtOAc and filter through a pad of diatomaceous earth. Concentrate the filtrate in vacuo to provide a i-esidue. Subject the residue to C- 18 reverse phase chromatography eluting with a gradient from 0% to 100% of (0. 1% formic acid in acetonitrile) in (0. 1% formic acid in water), to give the title compound (0.35 g, 14%). MS (ES) m/z = 198 (M¡ÀH)., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; BASTIAN, Jolie Anne; CLAYTON, Joshua Ryan; COATES, David Andrew; SALL, Daniel Jon; WOODS, Timothy Andrew; (58 pag.)WO2018/13486; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics