Heterocyclic Building Blocks-Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.388109-26-0,Ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate,as a common compound, the synthetic route is as follows.

O1 161 Step 1: i?o a solution of eth I 3-oxotetrahvdro2i 1.p ran-4-?carhoxvlate (1 0 g, 5.8mmo )in 1X?M (30 mu was added D1PI.A 1 .22 ml., 6.97 mmcl) and FfO (1 08 ml., 6.39mmoi at 78 C. then it us warmed up to room temperature and stirred at roomtemepemature fhr 2 h, the o1ution as diluted with DCM, ashcd with Sat. aH(O, brine.dried and concentated to give eih3 I 5?1((trifluoronieth l)sulton I oxy).?3,6?dih dio-21 lp mam4-cai boxy late as crude product (2 ,

388109-26-0, As the paragraph descriping shows that 388109-26-0 is playing an increasingly important role.

Reference£º
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; METCALF, Brian W.; WO2015/116061; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

223734-62-1, 2-((S)-Dec-1-yn-5-yloxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Preparation of chiral benzyl alkynol (3).; Table 2Triethylamine 101.19 0.68 g 0.0068Toluene NA 10 ml NAProcedure: A 50-mL, two-necked, round-bottomed flask equipped with a magnetic stirrer and stir bar was charged with zinc triflate (3.17 g, 0.0087 mol) and (+)-N-methylephedrine (1.22 g, 0.0068 mol) in toluene (5 mL). To this mixture triethylamine was added (0.68 g, 0.0068 mol) and this gelatinous mixture was stirred at ambient temperature for 1 -2 h. To this mixture was then added a solution of alkyne (1.57 g, 0.0065 mol) in toluene (4 mL), stirred at ambient temperature for 15-30 minutes followed by addition of a solution of aldehyde (2) (0.50 g, 0.0026 mol in 1-2 mL toluene). Progress of the reaction was monitored by TLC (Note 1). After stirring the mixture at room temperature for 16 h, TLC indicated completion of reaction. The reaction mixture was quenched by slow addition of water (10 mL). This was stirred for 5-10 minutes and organic layer containing desired compound was separated. The aqueous layer was extracted with ethyl acetate (10 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo to obtain a crude product. The crude product wa~ purified by column chromatography using 250-400 mesh silica gel. A solvent gradient of ethyl acetate in hexanes (5-20%) was used to elute the product from the column. All fractions containing the desired pure product were combined and concentrated in vacuo to give pure chiral benzyl alkynol (3, 700 mg, -70%). The structure was consistent with spectral data.1H NMR (CDC13, 300 MHz) delta 0.84 (t, 3H, J = 6 Hz), 1.25 – 1.82 (m, 17H), 2.28 (t, 1H, J = 6 Hz), 2.34 -2-42 (m, 2H), 3.42 -3.52 (m, 1H), 3.61 – 3.74 (m, 3H), 3.78 (s, 3H), 3.81 -3.95 (m, 1H), 4.61 (s, 2H), 4.68 (m, 1H), 4.94 – 5.01 (m, 2H), 5.62 (br s, 1H), 5.97 – 6.07 (m, 1H), 6.76 (d, 1H, J= 8 Hz), 7.16 -7.27 (m, 1H), 7.38 -7.43 (m, 1H); 13C NMR (CDC13, 75 MHz) 84.75, -4.38, -3.49, 14.12, 14.16, 14.84, 15.52, 18.06, 18.38, 20.04, 20.24, 22.70, 24.76, 25.25, 25.56, 25.72, 25.94, 29.67, 31.22, 31.28, 32.05, 32.11, 32.65, 33.41, 34.01 , 35.08, 52.22, 62.36, 62.84, 63.09, 66.04, 75.41, 76.44, 76.68, 80.83, 81.22, 85.57, 86.01, 97.31, 98.85, 110.89, 1 14.80, 119.77,1 19.82, 125.56, 127.11, 127.16, 136.46, 136.52, 142.66, 142.73, 155.83, 169.68; MS: (M+Na) 495.6.Note 1 : Completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent: 20% ethyl acetate in hexanes., 223734-62-1

As the paragraph descriping shows that 223734-62-1 is playing an increasingly important role.

Reference£º
Patent; UNITED THERAPEUTICS CORPORATION; BATRA, Hitesh; PENMASTA, Raju; SHARMA, Vijay; TULADHAR, Sudersan M.; WALSH, David A.; WO2011/153363; (2011); 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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

Compound 10-rac (100 mg, 0.28 mmol) and 37 4-bromotetrahydropyran (94 mg, 0.56 mmol) were dissolved in 5mL 31 DMF, and then the solution was added with 25 K2CO3 (78 mg, 0.56 mmol) and reacted at 90C for 40 h. After the reaction finished, the mixture was poured into water and extracted with EtOAc (40 mL¡Á3). The ethyl acetate layers were combined and washed with water and saturated salt solution, then dried over anhydrous sodium sulfate and filtered, and the filtrate was vacuum concentrated to give a crude product, which was purified by a preparation plate to give Compound 3a-rac (65 mg, 56.1% yield)., 25637-16-5

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

Reference£º
Patent; Ginkgo Pharma Co., Ltd.; CHEN, Li; ZHAI, Peibin; SHAO, Qing; WU, Jin; LI, Xiaowen; (46 pag.)EP3492467; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) 4-(p-Tosyloxy)tetrahydro-2H-pyran To an ice-cooled solution of tetrahydro-2H-pyran-4-ol (15g, 0.147mol) in dichloromethane (200ml) was added pyridine (36ml, 0.441mol) followed by 4-methylbenzenesulfonyl chloride (56g, 0.294mol), portionwise. The resultant mixture was stirred at room temperature overnight. After this time, the mixture was partitioned between 2N aqueous hydrochloric acid solution and dichloromethane. The aqueous portion was further extracted with dichloromethane and the organic fractions were combined and washed with brine. After drying over sodium sulphate and filtration, the solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel using a gradient elution with diethyl ether:hexane (50:50, by volume) changing to diethyl ether:hexane (100:0, by volume). This produced the title compound as a colourless oil which solidified upon scratching the walls of the flask (30.3g). LRMS m/z = 274.4 (m+ NH4)+ 1H-NMR (CDCl3): delta =1.6-1.9 (m,4H), 2.4 (s,3H), 3.4-3.5 (m,2H), 3.8-3.9 (m,2H), 4.6-4.7 (m,1H), 7.2-7.4 (m,2H), 7.7-7.8 (m,2H)., 2081-44-9

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

Reference£º
Patent; Pfizer Limited; PFIZER INC.; EP962457; (1999); 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.

14774-37-9, To a solution of 97 g (810 mmol) of Compound 6 (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 7 as white crystalline solid. Yield: 99%, ES-MS: m/z 271 [M+H]; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.19-1.35 (2H, m), 1.54-1.63 (2H, m), 1.85-2.02 (1H, m), 2.45 (3H, s), 3.28-3.39 (2H, m), 3.86 (2H, d, J=6.60 Hz), 3.93 (2H, dd, J=11.37, 4.52 Hz), 7.35 (2H, d, J=9.29 Hz), 7.78 (2H, d, J=8.31 Hz).

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/71196; (2011); 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.127956-11-0,Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate,as a common compound, the synthetic route is as follows.

Example 204B 3,3-Dimethyl- l,5,9-trioxa-spiro[5.5]undecane-7-carboxylic acid methyl ester A mixture of Example 204A (5 g, 31 mmol), 2,2-dimethyl-propane-l,3-diol (4.27 g, 41 mmol) and toluene-4-sulfonic acid (200 mg) in toluene (60 mL) was refluxed overnight using Dean- Stark trap. After cooling to room temperature, the reaction mixture was quenched with a saturated NaHC(? (100 mL) solution. The aqeous layer was extracted with ethyl acetate (200 mL). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by column chromatography (petroleum ether/ethyl acetate: 10/2) to provide the title compound (5 g, 65%) as a red oil.

127956-11-0, The synthetic route of 127956-11-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; WANG, Xueqing; MEYER, Michael; YAO, Betty; GUO, Tao; WEI, Guo Ping,Robert; WANG, Lijuan, Jane; WO2013/10453; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 100-mL round-bottom flask was placed a solution of 1-(tetrahydro-2H-pyran-4-yl)ethan-1-one (10 g,78.0 mmol) in THF (200 mL) then the solution was cooled to 0C and NaBH4 (1.50 g,39.5 mmol) was added. The reaction was stirred for 30 mm at 0C,quenched by the addition of water,and extracted withEtOAc. The organic extracts were combined and concentrated under reduced pressure affording 10 g (98%) of the title compound as colorless oil. Mass Spectrum (LCMS,ESI pos):Calcd. for C7H15O2: 131.1 (M+H); Found: 131.2.

137052-08-5, 137052-08-5 1-(Tetrahydro-2H-pyran-4-yl)ethanone 9877365, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (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.61363-56-2,2H-Pyran-3,5(4H,6H)-dione,as a common compound, the synthetic route is as follows.

61363-56-2, EXAMPLE 34 5-(2,1,3-benzoxadiazol-5-yl)-5,10-dihydro-1H,3H-dipyrano[3,4-b:4, 3-e]pyridine-4,6(7H,9H)-dione A mixture of tetrahydropyran-3,5-dione (Terasawa, J. Org. Chem. (1977), 42, 1163-1169) (0.27 g, 2.4 mmol), 2,1,3-benzoxadiazole-5-carboxaldehyde (Gasco, A. M. Eur.J.Med.Chem.Chim.Ther. (1996), 31,3-10) (0.54 g, 2.9 mmol) and the product from Example 11C (0.27 g, 2.4 mmol) in ethanol (3 mL) was processed as described in Example 29 to provide the title compound (0.088) as a solid. mp>260 C.; MS (ESI(-)) m/z 338 (M-H)31; H NMR (DMSO-d6) delta 4.08 (s, 4H), 4.54 (AB q, 4H), 5.06 (s, 1H), 7.61 (m, 2H), 7.97 (d, 1H), 10.23 (bs, 1H); Anal. Calcd for C17H13N3O50.5 C2H6O: C, 59.15; H, 4.26; N,11.83. Found: C, 59.09;H, 4.32; N, 11.99.

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

Reference£º
Patent; Abbott Laboratories; US6642222; (2003); B2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125995-03-1, Atorvastatin lactone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Form A atorvastatin magnesiumA 6.0 g sample of the lactone form of atorvastatin (United States Patent No. 5,273,995) was dissolved in 100 mL of methanol at room temperature. Approximately 11.8 mL of 1 N NaOH (1.05 mol equivalents) was then added to the mixture. The solution was then stirred at 50 0C for approximately 1 hour. A solution of 1.19g MgCI2-SH2O in 5 mL of H2O (0.55 mol equivalents) was then slowly added to the reaction mixture. The mixture was then cooled to room temperature and the resulting precipitate was removed by vacuum filtration through a 0.45-um nylon membrane filter. Approximately 100 mL of H2O was then slowly added to the filtered solution, which caused a white precipitate to form. The resulting suspension was then stirred for approximately 30 minutes. The solid sample was then isolated by vacuum filtration. The filtered solid was then dried under vacuum at 700C for approximately 2 hours to afford 5.8 g of Form A atorvastatin magnesium. Form B atorvastatin magnesiumA 50 mg sample of Form A atorvastatin magnesium (prepared as described above) was slurried in 0.25 mL of ortho-xylene at 45 oC for 28 days using magnetic stirring at 400 rpm. The solid sample was then isolated by centrifuge filtration through a 0.45-mum nylon membrane filter. The filtered solid was then air dried under ambient conditions for approximately 5 hours to afford Form B atorvastatin magnesium., 125995-03-1

125995-03-1 Atorvastatin lactone 6483036, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; PFIZER PRODUCTS INC.; WO2007/57755; (2007); 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.85064-61-5,Tetrahydropyranyl-4-acetic acid,as a common compound, the synthetic route is as follows.

A solution of methyl 2-amino-5-iodobenzoate (7.02 g, 25.3 mmol) and 2-(tetrahydro-2H-pyran-4-yl)acetic acid (3.76 g, 26.1 mmol) in pyridine (25 mL) was stirred at ?-40¡ã C. under argon while POCl3 (2.58 g, 27.8 mmol) was added dropwise over 3 minutes. The cold bath was immediately removed and the reaction was allowed to stir for 1 hour. The reaction was then diluted with water (75 mL) and extracted with DCM (75 mL). The combined orange organic layers were washed with 6 M aqueous HCl (50 mL), 1 M aqueous HCl (50 mL), and 2 M aqueous K3PO4 (50 mL), dried (Na2SO4), filtered, and concentrated to provide the title compound as an orange solid., 85064-61-5

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics