Day: October 13, 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1172623-99-2,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Step O: tert-Butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl]carbamate To 46.8 kg (142 mol) of tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbamate in a stirred vessel was added acetonitrile (150 kg), acetic acid (50 kg), and water (25 kg). After dissolving at room temperature, the solution was cooled to 0 C. and RuCl3.3H2O (250 g, 956 mmol) in water (50 kg) was added under nitrogen. Then, NaBrO3 (11.7 kg, 77.5 mol) was added in six portions every 1.5 h under nitrogen. After stirring at 0 C. for 6 h, 2-propanol (31 kg) was added over 30 min. at 0 C. Then, water (720 kg) was added at this temperature over 5 h. The resulting slurry was stirred overnight, filtered, and cake washed with water. The solids were then dried under vacuum at 40-60 C. to give tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl]carbamate.

1172623-99-2, The synthetic route of 1172623-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Merck Sharp & Dohme Corp; Merck Sharp & Dohme Ltd.; Arroyo, Itzia Z.; Krueger, Davida; Chen, Ping; Moment, Aaron J.; Biftu, Tesfaye; Sheen, Faye; Zhang, Yanfeng; US9181262; (2015); B2;,
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.585-88-6,Maltitol,as a common compound, the synthetic route is as follows.,585-88-6

Substrate specificity of CMM-forming enzyme of the present invention was investigated using various saccharides as substrates. Substrate solutions were prepared by dissolving maltose, maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, neotrehalose, trehalose, kojibiose, nigerose, isomaltose, isomaltotriose, panose, isopanose, maltitol, maltotriitol, alpha-, beta-, or gamma-cyclodextrin, amylose, soluble starch, glycogen, pullulan or dextran into water. Each substrate solution was admixed with acetate buffer (pH 6.0) and CaCl2 to give final concentrations of 20 mM and 1 mM, respectively. Then, each resulting substrate solution was further admixed with one unit/g-substrate, on a dry solid basis, of the purified preparation of CMM-forming enzyme, obtained by the method in Experiment 4. Substrate concentration was set to 2% (w/v) and followed by the enzyme reaction at 40C and pH 6.0 for 24 hours. Action and the specificity of the enzyme on these saccharides were confirmed by analyzing the reaction mixture before and after the reaction by TLC described in Experiment 1. The results are in Table 5; As is evident from the results in Table 5, CMM-forming enzyme of the present invention acts on maltotetraose, maltopentaose, maltohexaose, and maltoheptaose, and slightly on maltotriose among saccharides tested. Further, CMM-forming enzyme of the present invention acts on amylose, starch, and glycogen. From the results, it was revealed that the enzyme acted on alpha-1,4 glucans having a glucose polymerization degree of 3 or higher.

The synthetic route of 585-88-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; KABUSHIKI KAISHA HAYASHIBARA SEIBUTSU KAGAKU KENKYUJO; EP1674474; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-94-5, 4-(Iodomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2 g (1 0.3 mmol) 4-( 4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole and 2.9 mL (20.6mmol) 4-(iodomethyl)-tetrahydro-2H-pyran are dissolved in 200 mL DMF and 4.274 g (30.9s mmol) K2C0 3 are added. The mixture is shaken at 80″C for 5 h. After cooling to r.t. the mixture isfiltered, the filtrate is concentrated in vacuo to approximately 60 mL. The product is separatedusing HPLC-MS (Gilson, mass flow 120 mL/min, 10 lJ.m, 200g Sunfire RP18, ACN/waterfTFA).The product fractions arc combined and frecze-d1icd to yield 115 mg product (3.8 %) R6.3., 101691-94-5

The synthetic route of 101691-94-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140081; (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.14774-37-9,Tetrahydropyran-4-methanol,as a common compound, the synthetic route is as follows.

To a solution of 116 mg (1.00 mmol) of 4-(hydroxymethyl)tetrahydropyran from Example 77A in 2 mL of CH2Cl2 was added 424 mg (1.0 mmol) of the Dess-Martin periodinane. The mixture was stirred at ambient temperature for 1 h, then filtered through diatomaceous earth. The filter cake was washed with about 3 mL of CH2Cl2, then the tilted aldehyde solution was used directly in the next step.

14774-37-9, The synthetic route of 14774-37-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kosogof, Christi; Liu, Bo; Liu, Gang; Liu, Mei; Nelson, Lissa T. J.; Serby, Michael D.; Sham, Hing L.; Szczepankiewicz, Bruce G.; Xin, Zhili; Zhao, Hongyu; US2005/171131; (2005); A1;,
Tetrahydropyran – Wikipedia
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

A solution of (+/-)-1-(1-napthyl)ethanol XIII (20.2 g, 117.29 mmole) in tert- butyl methyl ether (50 ml) was added to a solution of the anhydride VIII (20 g, 117.50 mmole) in terf-butyl methyl ether (50 ml) at – 78 C under an atmosphere of nitrogen. DABCO (3.2 g, 28.53 mmole) was added to it and the reaction mixture was maintained at this temperature for 2 h when the reaction was complete as indicated from the TLC.An aqueous solution of citric acid was added to the reaction mixture and it was allowed to warm up to room temperature. The organic layer was washed with an aqueous solution of citric acid (3 chi 50 ml), water (3 * 50 ml) and brine (3 chi 50 ml), dried over sodium sulfate and concentrated to give the ester XII; yield 40 g, quantitative. The crude product was carried on to the following step without further purification.

185815-59-2, 185815-59-2 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione 11480690, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Dr. Braja Sundar Pradhan; WO2012/93411; (2012); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4295-99-2, 4-Cyanotetrahydro-4H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 2.46 M n-butyllithium in hexanes (29 mL, 71 mmol) was added dropwise to a stirred solution of (S)-2-(chloromethyl)oxirane (6.0 g, 64.8 mmol) and oxane-4- carbonitrile (8.4 g, 75.6 mmol) in THF (70 mL) at -78oC. The mixture was stirred at -78oC for two hours and then stirred overnight at room temperature. The mixture was quenched by the addition of saturated ammonium chloride, and extracted twice with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified via MPLC eluting with 20% ethyl acetate in petroleum ether to afford (S)-4-(oxiran-2- ylmethyl)tetrahydro-2H-pyran-4-carbonitrile (4.5 g, 42%) as a colorless liquid.

4295-99-2, 4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; TAYLOR, Clarke, B.; VANHUIS, Chad, A.; (410 pag.)WO2016/201225; (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.5631-96-9,2-(2-Chloroethoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

5631-96-9, Add cesium carbonate (725.82 g, 2.23 mol) and 2-(2-chloroethoxy)tetrahydro-2H- pyran (183.37 g, 167.01 mL, 1.50 equiv) to a solution of 6-[1-[1-(5-hydroxy-2- pyridyl)pyrazol-3 -yl]ethyl] -3 -(2-trimethylsilylethoxymethyl)- 1,3 -benzothiazol-2-one (400g, 742.56 mmol) in acetonitrile (2 L). Stir the mixture at 90 C for 3 h. Cool down the reaction and add cyclohexane (4 L) and water (4 L) and separate phases. Re-extract the aqueous layer with cyclohexane (2.5 L) and evaporate the combined organic layers to afford the desired compound as a brown oil (420 g, 8 1%). M+1597.

As the paragraph descriping shows that 5631-96-9 is playing an increasingly important role.

Reference£º
Patent; ELI LILLY AND COMPANY; GARDINIER, Kevin Matthew; GERNERT, Douglas Linn; HAHN, Patric James; HOLLINSHEAD, Sean Patrick; KHILEVICH, Albert; MAYHUGH, Daniel Ray; ORNSTEIN, Paul Leslie; PORTER, Warren Jaye; REEL, Jon Kevin; SCHKERYANTZ, Jeffrey Michael; SPINAZZE, Patrick Gianpietro; STEVENS, Freddie Craig; WITKIN, Jeffrey Michael; (199 pag.)WO2015/183673; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4677-20-7, 4-(2-Bromoethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4677-20-7

5-Ethyl-1 -methyl-1H-pyrazol-3-amine hydrogen chloride (1/1) (purchased from Enamine, 1.00 g, 6.19 mmol), 4-(2-bromoethyl)oxane (CAS 4677-20-7, 310, 2.1 mmol), potassium carbonate (1.14 g, 8.25 mmol) and potassium iodide (34.2 mg, 206 pmol) were dissolved in 1 1 ml_ acetonitrile and the mixture was stirred for 10 min at 1 10’O in the microwave. The reaction mixture was cooled down to rt and concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate twice. The combined organic layers were filtered through a waterresistant filter and the filtrate was concentrated under reduced pressure. The crude product was purified by HPLC under basic conditions to give 220 mg of the title compound (88% purity). LC-MS (Method2): Rt = 0.92 min; MS (ESIpos): m/z = 237 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) d [ppm] = 1.04 – 1.26 (m, 5H), 1.40 (q, 2H), 1.50 – 1.62 (m, 3H), 2.40 – 2.48 (m, 2H), 2.96 (br t, 2H), 3.25 (td, 2H), 3.46 (s, 3H), 3.81 (dd, 2H), 4.79 (br s, 1H), 5.22 (s, 1H).

The synthetic route of 4677-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; THEDE, Kai; MENGEL, Anne; CHRIST, Clara; KUHNKE, Joachim; JOHANNES, Sarah, Anna, Liesa; BUCHGRABER, Philipp; KLAR, Ulrich; SACK, Ulrike; KAULFUSS, Stefan; FERNANDEZ-MONTALVAN, Amaury, Ernesto; WERBECK, Nicolas; MOeNNING, Ursula; NOWAK-REPPEL, Katrin; MORTIER, Jeremie, Xavier; MCCARREN, Patrick, Ryan; SERRANO-WU, Michael, H.; LEMKE, Chris; MCKINNEY, David; FITZGERALD, Mark; NASVESCHUK, Christopher; LAZARSKI, Kiel; FERRARA, Steven, James; FURST, Laura; WEI, Guo; HARVEY, Rebecca, Ann; PAYNE, Daniel; PESNOT, Thomas; WILSON, Craig; (464 pag.)WO2019/96914; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1240390-36-6, tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3 tert-Butyl (3R,4R)-4-(7-(6-(2H-1,2,3-triazol-1-yl)pyridin-2-ylcarbamoyl)thieno[3,2-d]pyrimidin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate To a suspension of N-(6-(2H-1,2,3-triazol-1-yl)pyridin-2-yl)-2-chlorothieno[3,2-d]pyrimidine-7-carboxamide (0.13 g, 0.38 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.12 g, 0.56 mmol) in dioxane (3 mL) was added DIPEA (0.20 mL, 1.12 mmol). The reaction mixture was heated at 115 C. overnight. The reaction mixture was cooled then diluted with EtOAc, washed with aqueous sodium carbonate, then brine, and then dried over anhydrous Na2SO4. The organic phase was concentrated and purified by chromatography (silica, 40 g, EtOAc) to give tert-butyl (3R,4R)-4-(7-(6-(2H-1,2,3-triazol-1-yl)pyridin-2-ylcarbamoyl)thieno[3,2-d]pyrimidin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate (0.065 g, 0.12 mmol, 32.3%) as a white solid. LCMS m/z [M+H]=538., 1240390-36-6

1240390-36-6 tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate 68077633, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Hoffmann-La Roche Inc.; Chen, Shaoqing; Hermann, Johannes Cornelius; Le, Nam T.; Lucas, Matthew C.; Padilla, Fernando; US2013/178460; (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.713-95-1,6-Heptyltetrahydro-2H-pyran-2-one,as a common compound, the synthetic route is as follows.,713-95-1

4,4-Diethoxybut-1-yne 5 (6.66 g, 44.1 mmol) in dry THF (120 mL) was cooled to -78 C. nBuLi (27.7 mL of a 1.59 M solution in hexanes, 44.0 mmol) was added dropwise (2 min), which gave a pale yellow solution, that was stirred (10 min). A solution of delta-dodecalactone 4 (6.99 g, 35.2 mmol) in dry THF (30 mL) was added dropwise (5 min) and the solution was stirred (1 h). The reaction was quenched with saturated aqueous NH4Cl and allowed to warm to room temperature. This mixture was diluted with EtOAc and H2O and the organic layer was separated. The aqueous phase was re-extracted (2 times) with EtOAc. The combined organics were washed sequentially with saturated aqueous NaHCO3, saturated aqueous NaCl, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (EtOAc/hexanes, gradient; 10:90, 15:85; 25:75 then 30:70) to yield alkyne 6 (10.8 g 90%) as a clear yellow oil: Rf 0.34 (30:70 EtOAc/hexanes); IR (neat) 3448, 2937, 2858, 2217, 1674, 1457, 1373, 1346, 1228, 1162, 1120, 1063 cm-1; 1H NMR (CDCl3, 400 MHz) delta 0.85-0.90 (m, 3H, CH3), 1.20-1.25 (m, 6H, 2 X O-CH2-CH3), 1.25-1.53 (m, 15H), 1.61 (b s, 1H, OH), 1.66-1.89 (m, 2H), 2.58 (t, J = 7.2 Hz, 2H), 2.70 (d, J = 5.6 Hz, 2H), 3.51-3.61 (m, 2H) 3.64-3.73 (m, 2H), 4.70 (t, J = 5.6 Hz, 1H); 13C NMR (CDCl3, 100 MHz) delta 14.02, 15.12, 20.00, 22.58, 25.39, 25.59, 29.22, 29.57, 31.76, 36.47, 37.45, 45.25, 62.08, 71.36, 81.73, 89.25, 100.96, 187.95; HRMS (EI) m/z 339.2516. C20H35NO4 [M-1] +¡¤ requires 339.2530.

As the paragraph descriping shows that 713-95-1 is playing an increasingly important role.

Reference£º
Article; Eldridge, Cecily; Quek, Gracia; Sako, Michael; Ryan, John H.; Saubern, Simon; Chebib, Mary; Macdonald, James M.; Tetrahedron; vol. 74; 12; (2018); p. 1245 – 1252;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics