Heterocyclic Building Blocks-Tetrahydropyrans

14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Synthesis of B-3Prepared as described by adaptation of the following literature reference:Radziszewski, J.G. et al. J. Am. Chem. Soc. 1993, 115, 8401.To a solution of 97 g (810 mmol) of compound B-2 in 2-methyltetrahydrofuran (190 mL) are added 165 mL of 50% aqueous NaOH solution. To this stirred suspension is added dropwise with cooling a solution of p-toluene-sulfonylchloride (283 g, 1.46 mol) in 2- methyltetrahydrofuran (280 mL). The reaction is stirred at 30-35 C for 18 h. The suspension is poured into a mixture of ice-water (280 mL) and aqueous HCl solution (37%, 203 mL). After addition of methylcyclohexane (1.4 L) and further ice-water (0.2 L), the reaction mixture is stirred for 2 h in an ice-bath. The resulting crystalline precipitate is isolated by filtration and washed with methylcyclohexane (0.5 L) and water (0.5 L).Drying under reduced pressure at 40 C gave 216 g of compound B-3 as white crystalline solid. Yield: 99%, ES-MS: m/z 271 [M+H]; *H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.19 – 1.35 (2 H, m), 1.54 – 1.63 (2 H, m), 1.85 – 2.02 (1 H, m), 2.45 (3 H, s), 3.28 – 3.39 (2 H, m), 3.86 (2H, d, J=6.60 Hz), 3.93 (2 H, dd, J=l 1.37, 4.52 Hz), 7.35 (2 H, d, J=9.29 Hz), 7.78 (2 H, d, J=8.31 Hz)

14774-37-9, 14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HICKEY, Eugene Richard; RIETHER, Doris; ERMANN, Monika; WO2012/12307; (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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

A solution of 2,2-dimethyltetrahydropyran-4-one (133) (115 g, 0.9 mol, 1.0 eq.) in anhydrous THF (600 mL) was cooled to -78 C and to it was added LDA (2.0 M, 538 mL, 1.08 mol, 1.2 eq.) drop wise under N2 keeping the internal temperature below -65 C. The resulting solution was stirred at -78 C for 20 min. A solution of N-phenyl- bis(trifluoromethanesulfonimide) (353 g, 0.99 mol, 1.1 eq.) in anhydrous THF (1900 mL) was added to the above solution slowly keeping the internal temperature below -65 C. The reaction mixture was warmed to room temperature slowly and stirred overnight. The reaction was quenched with saturated aqueous sodium bicarbonate solution, and extracted with MTBE (2 L X 2). The combined organic layers was washed with 10% aqueous NaOH solution (1 L X 2), brine (500 mL X 2), dried over Na2S04, filtered and concentrated to give crude title triflate product mixture as dark brown oil. The crude product was extracted with hexanes (2 L X 5) and the combined hexanes extracts was purified by column chromatography (directly loaded onto silica gel, Hexanes? 15% ethyl acetate in hexanes, R/= 0.6, visualized with KMn04 stain) to give 200 g of the triflate product mixture (134) (a mixture of 2,2-dimethyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate and 6,6-dimethyl-3 ,6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate ratio = 80.6: 19.4 by GCMS) as a light yellow liquid (~ 90% purity by GC-MS and 1H NMR). This was taken to the next step without further purification.

1194-16-7, 1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; ALLEN, Jennifer R.; CHEN, Jian J.; FROHN, Michael J.; HU, Essa; LIU, Qingyian; PICKRELL, Alexander J.; RUMFELT, Shannon; RZASA, Robert M.; ZHONG, Wenge; WO2011/143365; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

61363-56-2,61363-56-2, 2H-Pyran-3,5(4H,6H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 30 4-(4-bromo-3-chlorophenyl)-1-methyl-1,2,4,9-tetrahydropyrano[3,4-b]pyrazolo[4,3-e]pyridine-3,5(6H,8H)-dione 2H-Pyran-3,5(4H,6H)-dione (0.057 g, 05 mmol), 3-chloro4-bromo-benzaldehyde (0.11 g, 0.5 mmol), and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.056g, 0.5 mmol) were processed as described in Example 26C to provide 0.145 g of the title compound. 1H NMR (300 MHz, DMSO-d6)6 3.5 (s, 3H), 4.0 (s, 2H), 4.52 (q, 2H), 4.92 (s, 1H), 7.03 (dt, 1H), 7.32(t, 1H), 7.6 (dd, 1H), 9.62 (s, 1H), 10.1 (s, 1H); MS (ESI-) m/z 410 (M+H:) Anal. calcd for C16H13N3BrClO3: C, 46.80;H,3.19; N, 10.23. Found: C, 46.77;H, 3.43; N, 10.27.

As the paragraph descriping shows that 61363-56-2 is playing an increasingly important role.

Reference£º
Patent; Drizin, Irene; Altenbach, Robert J.; Carroll, William A.; US2002/7059; (2002); 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

In a round bottom flask under argon was placed tetrahydrofuran (30 mL) and 1,1,1,3,3,3-hexamethyldisilazane (1.50 mL, 7.13 mmol) and it was cooled to -78 C. in a dry ice/acetone bath. To this cooled solution was then added n-butyl lithium (2.5 M solution in hexanes, 2.70 mL, 6.69 mmol) and it was stirred for 15 min at -78 C. To this cooled solution was then added a solution of (3-methyl-4-methylsulfanyl-phenyl)-acetic acid methyl ester (1.34 g, 6.37 mmol) in tetrahydrofuran (20 mL) dropwise. This was then stirred for 10 min at -78 C. then at 0 C. for 1 h which resulted in an gold colored solution. After such time, the reaction was cooled back to -78 C. and a solution of 4-iodomethyl-tetrahydro-pyran (prepared as in PCT WO 2003/095438 A1, Example 20, 1.73 g, 7.64 mmol) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1.17 mL, 9.56 mmol) was added dropwise at -78 C. The reaction was then allowed to slowly warm to 0 C. and it was stirred for 16 h. After such time, the reaction was diluted with ethyl acetate (250 mL) and washed with a saturated aqueous ammonium chloride solution (1¡Á50 mL) followed by a saturated sodium chloride solution wash (1¡Á50 mL). The organics were dried over sodium sulfate, filtered and then concentrated with silica gel (4 g) in vacuo and purified on Biotage Flash chromatography system (40M column, silica gel, 10% ethyl acetate/hexanes) to afford 2-(3-methyl-4-methylsulfanyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (1.49 g, 76%) as a gold oil., 101691-94-5

As the paragraph descriping shows that 101691-94-5 is playing an increasingly important role.

Reference£º
Patent; Berthel, Steven Joseph; Kester, Robert Francis; Murphy, Douglas Eric; Prins, Thomas Jay; Ruebsam, Frank; Sarabu, Ramakanth; Tran, Chinh Viet; Vourloumis, Dionisios; US2008/21032; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1172623-99-2, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Tert-butyl (2R,3S)-2-(2,5-difluorophenyl)-5-hydroxyltetrahydro-2H-pyran-3-ylcarbamate (2.33 g, 7.08 mmol) was dissolved in a mixed solution of 24 mL acetonitrile, 4 mL water and 4 mL acetic acid. Thereto was added an aqueous solution (4 mL) of ruthenium chloride hydrate (3.7 mg, 0.0142 mmol), and cooled to 0 C. Sodium bromate (535 mg, 3.54 mmol) was added, and stirred at low temperature for about 1.5 hours until the raw materials were completely reacted. To the reaction solution was added 120 mL water, stirred at 0 C overnight, and extracted with dichloromethane. The organic phase was washed with water, dried and concentrated, and then the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 10:1) to give the intermediate 1 tert-butyl (2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-ylcarbamate (1.71 g) as a white solid in 74% yield. 1H-NMR (400 MHz, CDCl3): delta=7.22(1H, m), 7.00(1H, m), 4.82 (1H, m), 4.63 (1H, m), 4.29(1H, d, J=16.2Hz), 4.11(1H, d, J=16.4Hz), 4.05 (1H, m), 3.05(1H, m), 2.85 (1H, m), 1.30 (9H, s)., 1172623-99-2

As the paragraph descriping shows that 1172623-99-2 is playing an increasingly important role.

Reference£º
Patent; Centaurus BioPharma Co., Ltd.; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; XU, Xinhe; SHEN, Yu; XIAO, Dengming; LUO, Hong; PENG, Yong; HAN, Yongxin; ZHANG, Aiming; YANG, Ling; (51 pag.)EP3257857; (2017); 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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A mixture of intermediate XIX.1 (500 mg; 1.21 mmol) and 4-iodomethyl-tetrahydropyrane (1.07 g; 4.73 mmol) in ACN (5.0 ml) is heated to 120 C. (microwave heating; closed vessel) for 7 h. Additional 4-iodomethyl-tetrahydropyran (1.07 g; 4.73 mmol) is added and the mixture is again heated to 120 C. (microwave heating; closed vessel) over night. Volatiles are evaporated and the crude product is purified by RP-HPLC (modifier: TFA) to yield the title compound. [0212] C25H40ClN4O5¡ÁC2F3O2 ESI Mass spectrum: m/z=511 [M]+, 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; KLEY, Joerg; FRATTINI, Sara; HAMPRECHT, Dieter; US2015/18315; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

K2C03 (0.16 g, 1 .20 mmol) followed by ethyl iodide (0.07 mL, 0.90 mmol) were added at RT to a solution of compound 67b (0.20 g, 0.60 mmol) in dry DMF (7 mL) and the reaction mixture was stirred at RT for 48 h. Crushed ice was added and the mixture was extracted with EtOAc. The organic phase was washed with water and brine, dried over Na2S04 and evaporated. The residue was purified by flash column chromatography [silica; hexane with 5% EtOAc]. White solid. Yield: 0.15 g (69%). HPLC (method 1 ): Rt = 2.67 min, m/z [M+H]+ = 362.0 (MW calc. 361.41 ). H NMR (400 MHz, DMSO-d6, delta ppm): 8.82 (s, 2H), 8.03 (d, 1 H, J = 1.96 Hz), 7.68-7.64 (m, 1 H), 7.48-7.43 (m, 1 H), 7.38-7.32 (m, 2H), 6.71 (d, 1 H, J = 8.1 Hz), 6.50-6.48 (m, 1 H), 4.22 (s, 2H), 4.03-3.98 (m, 2H), 1 .35-1 .32 (m, 3H), 1.10-1.02 (m, 4H).Prepared from compound 67b and 4-bromotetrahydro-2H-pyran in analogy to procedure 67c. White solid. Yield: 10 mg. MS: m/z: [M+H] = 418.1 (MW calc. 417.19)., 25637-16-5

25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; GRUeNENTHAL GMBH; KONETZKI, Ingo; JAKOB, Florian; WAGENER, Markus; WELBERS, Andre; HESSLINGER, Christian; (138 pag.)WO2017/108203; (2017); 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.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