Category: Tetrahydropyrans

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

A solution of 2 – ((1 H-pyrrolo [2,3 -b] pyridin-5- yl) oxy) -4- 5,Tetrahydro- [1,1′-biphenyl] -2-yl) methoxy) azetidin- 1 -yl) benzoic acid (50 mg, 0.089 mmol, 1.0 eq) and3-nitro-4-(((Tetrahydro-2H-pyran-4- yl) methyl) amino) benzenesulfonamide (31 mg, 0.098 mmol, 1.1 eq)8 mL of DCM, EDCI (34 mg, 0.18 mmol, 2.0 eq) and DMAP (13 mg, 0.107 mmol, 1.2 eq)at rt 7h. The reaction was stopped, poured into water and the organic phase was separated. The organic phase was dried over anhydrous sodium sulfate, spun dry and passed through a plug of PE / EA (v / v) =1/1 do eluent to obtain 35mg yellow powder product., 1228779-96-1

As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.

Reference£º
Patent; Sun Yat-sen University; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Kou Yuhui; Hu Bolin; Jiang Haigang; Ye Jiuyong; Liu Zhiqiang; Xie Hongming; Zhang Yingjun; Yan Ming; (39 pag.)CN106749233; (2017); 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.23462-75-1,Dihydro-2H-pyran-3(4H)-one,as a common compound, the synthetic route is as follows.

Dihydro-2//-pyran-3(4H)-one (100 mg, 1.00 mmol), /er/-butyl carbazate (145 mg, 1.10 mmol, Ll equiv) and acetic acid (0.280 niL, 4.99 mmol, 5 equiv) were combined in 1 ,2-dichloroethane(3 raL), stirred at ambient temperature for 10 minutes and treated with sodium triacetoxyborohydride (296 mg, 1,34 mmol, 1.4 equiv). After stirring for 1 hour, the mixture was poured into water and extracted with ethyl acetate (3 x 50 niL), The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo to provide the titled compound., 23462-75-1

23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP &; DOHME CORP.; BESHORE, Douglas, C.; KUDUK, Scott, D.; WO2010/123716; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 Methylmaganesium bromide (1.831 mL, 5.49 mmol) was added dropwise via syringe to a solution of dihydro-2H-pyran-3(4H)-one (500 mg, 4.99 mmol) in Diethyl ether (50 mL) at -20 C. and stirred at this temp for 1 hr before warming up to RT. The reaction was quenched with sat. ammonium chloride and extracted with ether. The organic layer was washed with brine, collected, dried over MgSO4, filtered and partially evaporated to give the crude product 3-methyltetrahydro-2H-pyran-3-ol (480 mg, 83% yield) as an oil. 1H NMR (400 MHz, CHLOROFORM-d) delta 3.90-3.81 (m, 1H), 3.55-3.50 (m, 1H), 3.40 (td, J=11.3, 2.8 Hz, 1H), 3.31 (d, J=11.3 Hz, 1H), 2.16 (br. s., 1H), 1.94-1.81 (m, 1H), 1.78-1.69 (m, 1H), 1.59-1.47 (m, 2H), 1.18-1.11 (m, 3H)., 23462-75-1

23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

40191-32-0, Tetrahydro-2H-pyran-4-carbonyl chloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,40191-32-0

Example 21Synthesis of N-(3-{3-[4-(1-aminocyclobutyl)phenyl]-2-(2-aminopyridin-3-yl)-3H-imidazo[4,5-b]pyridin-5-yl}phenyl)tetrahydro-2H-pyran-4-carboxamide hydrochlorideStep 1Synthesis of N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydro-2H-pyran-4-carboxamideTo a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (220 mg) and triethylamine (0.182 mL) in N,N-dimethylacetamide (1.5 mL) chilled to 0 C. was added tetrahydro-2H-pyran-4-carbonyl chloride (prepared from tetrahydro-2H-pyran-4-carboxylic acid (156 mg) and oxalyl chloride (0.15 mL) in dichloromethane (2.5 mL)) dropwise. After being stirred at room temperature for 1 h, the reaction mixture was diluted with ethyl acetate and washed with 1 M citric acid aqueous solution (3 times) then brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (10-100% ethyl acetate in hexanes) gave the product (267 mg, 81%). 1H-NMR (400 MHz, CDCl3) delta: 7.92-7.87 (m, 1H), 7.68-7.66 (m, 1H), 7.57-7.53 (m, 1H), 7.35 (t, 1H, J=7.6 Hz), 7.14 (br s, 1H), 4.10-4.03 (m, 2H), 3.46 (ddd, 2H, J=11.5, 11.5, 2.8 Hz), 2.51-2.42 (m, 1H), 1.97-1.80 (m, 4H), 1.34 (s, 12H); LCMS: 332 [M+H].

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

Reference£º
Patent; ArQuele, Inc.; US2012/329791; (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.127956-11-0,Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate,as a common compound, the synthetic route is as follows.

Step 2: 5-(Methoxycarbonyl)-tetrahydro-4-oxo-2H-pyran-3-carboxylic acid; Methyl tetrahydro-4-oxo-2H-pyran-3-carboxylate (18.6 mmol) is heated with a magnesium methyl carbonate solution (1.94M; 80 mL) at 120-1300C for 6 hours. After hydrolysis the crude product is extracted into ether, dried, and isolated. Crystallization from methanol gives the pure product. See Stiles, J. Am. Chem. Soc. 1959, 81, 2598.

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; SYNDAX PHARMACEUTICALS, INC.; WO2009/49018; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

40191-32-0,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.

Step 2 To a solution of 6-benzyl-4-((S)-pyrrolidin-3-yloxy)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine (420 mg, 1.35 mmol) in 4ml_ of CH2CI2 was added tetrahydro-pyran-4-carbonyl chloride (0.210 mL, 1.637 mmol) and Et3N (0.380 mL, 2.73 mmol). The reaction mixture was stirred at room temperature for 30 min then was quenched with H20, extracted with CH2CI2, filtered and evaporated under vacuum. Purification by flash-chromatography on silica gel (CH2CI2 / MeOH 95/5) gave [(S)-3-(6-benzyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidin-1-yl]-(tetrahydro-pyran-4-yl)-methanone (420 mg, 73% yield) as a yellow foam. 1H NMR (400 MHz, DMSO-d6, 298K) delta ppm 1.37-1.64 (m, 4H) 1.95-2.29 (m, 2H) 2.56-2.83 (m, 4H) 3.28-3.91 (m, 13H) 5.54-5.68 (m, 1 H) 7.24-7.36 (m, 5H) 8.54-8.59 (m, 1 H). LCMS: [M+H]+= 423.6, Rt(7)= 0.68.

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.28244-94-2,4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-¦Â-D-glucopyranoside,as a common compound, the synthetic route is as follows.

1,2,3,4,6-Penta-O-acetyl-D-glucopyranose S1 (10.0 g, 0.0267 mol) and p-thiocresol (4.0 g, 0.032 mol) was dissolved in CH2Cl2(100mL) in a flame dried flask under nitrogen atmosphere. Boron trifluoride diethyl etherate (5.60 mL, 0.04mol) was slowly added at 0 C. After stirring for 16 hours at room temperature, the reaction mixture was diluted with CH2Cl2(100mL), washed with NaHCO3 (100 mL ¡Á 2) and brine (100 mL), dried over anhydrous MgSO4, filtered, and then concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (EtOAc/Hexane = 0/1 to 1/2) to obtain 2,3,4-tri-O-acetyl-1-thio-beta-Dglucopyranoside S2.To a solution of compound S2 in methanol (100 mL) was added sodium methoxide (432.0 mg, 0.008mol) at room temperature under ambient atmosphere. After stirring for 4 hours, amberlite IR (120 H+) acid resin was added protionwise until the solution was neutralized. The mixture was filtered, concentrated under reduced pressure, and then volatiles were removed in vacuo to afford tetrol glycosideS3. To a solution of tetrol glucopyranoside S3 and benzaldehyde dimethyl acetal(6.10 g, 0.040 mol) in dried acetonitrile (100 mL) was added camphorsulfonic acid (0.620 g, 2.670 mmol) in a flame dried flask under nitrogen atmosphere. After stirring for 6 hours at room temperature, the reaction solution was diluted with ethyl acetate (100 mL), washed with NaHCO3 (50 mL ¡Á 2) and brine (50 mL), dried over anhydrous MgSO4, filtered, concentrated under reduced pressure, and then volatileswere removed in vacuo to obtain 4,6-O-benzylidine-D-glucopyranoside S4.To a solution of 4,6-O-benzylidine-D-glucopyranoside S4 in dried DMF (80 mL) was added benzyl bromide (7.0 mL, 0.059 mol) in a flame dried flask under nitrogen atmosphere. Sodium hydride (60% dispersion in mineral oil, 2.560 g, 0.064mol) was added portionwise and gradually in the reaction solution at 0 C. After s20stirring for 16 hours at room temperature, the mixture was diluted with ethyl acetate (100 mL), quenched by water (50 mL¡Á2) and washed with brine (50 mL), dried over anhydrous MgSO4, filtered, and then concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (EtOAc/ Hexane= 0/1 to 1/4) and then volatiles were removed in vacuo to acquire the benzyl glycoside S5 as a white solid.Compound S5 was dissolved in dried CH2Cl2(50 mL) in a flame dried flaskunder nitrogen atmosphere. Borane-tetrahydrofurane complex (1M in THF, 130 mL, 0.13 mol) and trimethyl silyltrifluoromethanesulfonate (2.30 mL, 0.013 mol) was added subsequently in the reaction solution at 0 C After stirring for 6 hours at 0oC, the reaction mixture was quenched by NaHCO3 (50 mL¡Á3), washed with brine (50 mL), dried over anhydrous MgSO4, filtered, and then concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (EtOAc/ Hexane= 0/1 to 1/2) and then volatiles were removed in vacuo to acquire the product (64) as white solid. [alpha]28D4.93 (c 0.58, CHCl3); 1H NMR (400 MHz, CDCl3) delta 7.42-7.27 (m, 17 H, Ph), 7.11 (d, J8.0 Hz, 2 H, Ph), 4.93- 4.83 (m, 3 H, PhCH), 4.76 (d, J10.4 Hz, 1 H, PhCH), 4.61 (d, J12.4 Hz, 2 H, PhCH and H-1), 3.89-3.83 (m, 1 H, H-6), 3.71 (t, J9.2 Hz, 1 H, H-3), 3.70-3.65 (m, 1 H, H-6), 3.55 (t, J9.2 Hz, 1 H, H-4), 3.45 (t, J9.2 Hz, 1 H, H-2),3.38-3.33 (m, 1 H, H-5), 2.33 (s, 3 H, Me), 1.89 (t, J6.8 Hz, 1 H, OH) ppm; 13C NMR: delta 138.3-137.8 (C), 132.5 (CH), 129.7 (CH), 129.4 (CH), 128.4-127.6 (CH), 87.7 (CH), 86.5 (CH), 81.0 (CH), 79.2 (CH), 77.6 (CH), 75.6 (CH2), 75.3 (CH2), 75.0 (CH2), 62.0 (CH2), 20.9 (CH3) ppm; HRMS (ESI, m/z) calcd for C34H36O5NaS [M + Na]+requires 579.2181, found 579.2183, 28244-94-2

The synthetic route of 28244-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Hsu, Mei-Yuan; Liu, Yi-Pei; Lam, Sarah; Lin, Su-Ching; Wang, Cheng-Chung; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1758 – 1764;,
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.720706-20-7,(4-Amino-4-tetrahydropyranyl)methanol,as a common compound, the synthetic route is as follows.

720706-20-7, To a stirred solution of 2, 4-dichloro-5-((4-methoxybenzyl) oxy) pyrimidine (2 g, 7.04 mmol) in isopropyl alcohol (30 mL) under an argon atmosphere were added diisopropylethylamine (2.4 mL, 14.08 mmol) and (4-aminotetrahydro-2H-pyran-4-yl) methanol (900 mg, 7.04 mmol) at room temperature. The reaction mixture was stirred at 120 oC for 48 h. After consumption of starting material (monitored by TLC), the volatile components were evaporated in vacuo. The crude material was purified by column chromatography using 20-30% EtOAc:hexanes to afford (4-((2-chloro-5-((4-methoxybenzyl) oxy) pyrimidin-4-yl) amino) tetrahydro-2H-pyran-4-yl) methanol (1 g, 38%) as a white solid. 1H NMR (CDCl3, 400 MHz): delta 7.66 (s, 1H), 7.30 (d, 2H), 6.94 (d, 2H), 5.47 (s, 1H), 5.03 (s, 2H), 4.60 (t, 1H), 3.87-3.83 (m, 5H), 3.80-3.73 (m, 2H), 3.68-3.60 (m, 2H), 1.97-1.87 (m, 4H); LCMS: 379.9 (M+1); (column; X-select CSH C-18 (50 ¡Á 3.0 mm, 3.5 mum); RT 3.07 min. 0.05% Aq TFA: CH3CN; 0.8 mL/min); TLC: 50% EtOAc:hexane (Rf: 0.3).

As the paragraph descriping shows that 720706-20-7 is playing an increasingly important role.

Reference£º
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/109109; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

83-87-4, (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

83-87-4, (1) Weigh the hydroxyacetylated glucose intermediate (35 g, 89.7 mmol) obtained in step (1)Triethylamine (4.75 g, 46.9 mmol),3,4-dimethoxyphenol (20G, 129.7 mmol),Sequentially added to dichloromethane (250mL) at 0 C conditions,Boron trifluoride ethyl ether silica gel (50 g)Then naturally warmed to room temperature for 9 hours; then the organic phaseWashed successively with saturated sodium bicarbonate, saturated brine, filtered,Concentrated, recrystallized from anhydrous methanol,A yield of 94.3% was obtained for 40.95 g of glycoside intermediate substituted at the position of glucose anomeric carbon.

As the paragraph descriping shows that 83-87-4 is playing an increasingly important role.

Reference£º
Patent; Dongying Daoyi Bio-pharmaceutical Technology Co., Ltd.; Weifang Hongnuo He Tai New Materials Technology Co., Ltd.; Li Fahui; (5 pag.)CN107151260; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 1.07 g (1.90 mmol) of the compound from Example 8A in 20 ml of DMF under argon were added 256 mg (2.28 mmol) of potassium tert-butoxide. After stirring at RT for 5 min, 408 mg (2.28 mmol) of 4-(bromomethyl)tetrahydropyran were added, and the mixture was stirred at bath temperature 100C. for 2 h. Subsequently, a further 136 mg (0.76 mmol) of 4-(bromomethyl)-tetrahydropyran were added and the mixture was stirred at bath temperature 100C. for another 2 h. After cooling to RT, the mixture was combined with the reaction mixtures from two similarly conducted prior experiments (batch size in each case 47 mg (0.08 mmol) of the compound from Example 8A). After removing the DMF, 60 ml of water and 60 ml of ethyl acetate were added to this combined mixture. After the phases had been separated, the aqueous phase was extracted once with 30 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated. The residue was taken up in a mixture of cyclohexane and ethyl acetate (9:1) and purified by means of column chromatography (120 g of silica gel, eluent: cyclohexane/ethyl acetate 9:1). 590 mg (47% of theory, purity 100%) of the title compound were obtained. [0384] 1H NMR (400 MHz, CDCl3): delta [ppm]=8.66 (s, 1H), 8.28 (d, 1H), 8.14 (dd, 1H), 7.95 (d, 2H), 6.92 (d, 2H), 4.78-4.62 (m, 2H), 4.21-4.13 (m, 1H), 4.03 (dd, 2H), 3.89-3.81 (m, 4H), 3.50-3.40 (m, 3H), 3.07-2.93 (m, 1H), 2.19-2.03 (m, 2H), 2.03-1.87 (m, 2H), 1.76 (dd, 2H), 1.72-1.61 (m, 1H), 1.47 (qd, 2H), 0.63-0.53 (m, 2H), -0.09 (s, 9H). [0385] LC/MS (Methode 1, ESIpos): Rt=1.51 min, m/z=560 [M+H]+., 125552-89-8

The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMANN, Andreas; BROHM, Dirk; JOeRISSEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (44 pag.)US2017/114049; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics