Heterocyclic Building Blocks-Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

c) To a solution of 425 mg (2.5 mmol) of ethyl 2-(tetrahydro-2H-pyran-4- yl)acetate in 10 mL of dry THF cooled at 05C under argon, a 2.71 mL of a solution of LiAII-U 1 M in THF was added. Bubbling was observed. It was stirred at room temperature for 30 min. Then it was quenched with wet EtAcO, dried with MgS04 and filtered through celite, washing with abundant EtAcO. After removing the solvent the desired compound, 2-(tetrahydro-2H-pyran-4-yl)ethanol, was obtained (300 mg, 93%).

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; DRACONIS PHARMA, S.L.; ALMIRALL, S.A.; TORRENS JOVER, Andoni; MERCE VIDAL, Ramon; CALDENTEY FRONTERA, Francesc Xavier; RODRIGUEZ GARRIDO, Antonio, David; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/37960; (2013); A1;,
Tetrahydropyran – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Tetraethyl 4-(2-Tetrahydro-2H-pyranyloxy)butylene-1,1-bisphosphonate (34). To a suspension of NaH (60% suspension in mineral oil, 900 mg, 22.0 mmol) in dry THF (20 mL) was added dropwise tetraethyl methylenebisphosphonate (6.46 g, 22.4 mmol). The resulting clear solution was stirred 15 min at room temperature, after which 2-(3-bromopropoxy)tetrahydro-2H-pyran (5.05 g, 22.6 mmol) was added dropwise. The reaction mixture was heated to reflux for 6 h, diluted with CH2Cl2 (75 mL) and washed with brine (2*50 mL), dried (MgSO4) and evaporated. It was used as such in the following step., 33821-94-2

The synthetic route of 33821-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TARGANTA THERAPEUTICS, INC.; US2010/113333; (2010); A1;,
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25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: In air, CuBr (7.1 mg, 0.05 mmol), PPh3 (17.03 mg, 0.065 mmol), LiOtBu(80 mg, 1mmol), and bis(neopentyl glycolato) diboron (168mg, 0.75 mmol ) were added to aSchlenk tube equipped with a stir bar. The vessel was evacuated and filled with argon(three cycles). DMAc (1 mL), alkyl halide (0.5 mmol) were added in turn by syringeunder an argon atmosphere (if the alkyl halide is a solid, it was added along with theCuBr). The resulting reaction mixture was stirred vigorously at 25 C for 18 h. Thereaction mixture was then diluted with EtOAc, filtered through silica gel with copiouswashings (petroleum ether to EtOAc), concentrated, and purified by columnchromatography., 25637-16-5

The synthetic route of 25637-16-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Lou, Xin; Zhang, Zhen-Qi; Liu, Jing-Hui; Lu, Xiao-Yu; Chemistry Letters; vol. 45; 2; (2016); p. 200 – 202;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

In a 500mL reaction flask, add intermediate V4 (24.5g, 32mmol, 1.0eq), intermediate VM4 (13g, 41mmol, 1.3eq) and 800mL dichloromethane, stir to dissolve, then add CDI (7.7g, 48mmol, 1.5eq ) And 2.5g DMAP, heated to 30-35 reaction,TLC monitors the reaction.After the reaction is completed, add 300mL of 10% acetic acid aqueous solution and stir for 30min to separate the organic phase.The organic phase was washed with saturated aqueous sodium bicarbonate solution (200 mL ¡Á 1) and saturated aqueous sodium chloride solution (200 mL ¡Á 1), dried over anhydrous sodium sulfate, filtered with suction, and the filtrate was concentrated under reduced pressure to obtain a crude solid product. The crude product was recrystallized with 300 mL of ethyl acetate and n-hexane (1: 1),29.2 g of solid product V5 was obtained.Yield: 87%.

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

Reference£º
Patent; Nantong Changyou Pharmaceutical Technology Co., Ltd.; Li Zebiao; Chen Dan; Wu Hongdang; Xu Xiaohong; Lin Yanfeng; (9 pag.)CN110878098; (2020); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

Preparation Example 50 To a solution of tetrahydro-2H-pyran-4-ol (1.00 g) in pyridine (10 mL) was added 4-methylbenzenesulfonyl chloride under ice-cooling, and the reaction mixture was stirred at room temperature for 3 days. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with 1 M hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure to obtain tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate (2.72 g) as a pale orange oil., 2081-44-9

The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Negoro, Kenji; Ohnuki, Kei; Yonetoku, Yasuhiro; Kuramoto, Kazuyuki; Urano, Yasuharu; Watanabe, Hideyuki; US2012/35196; (2012); A1;,
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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.,23462-75-1

A solution of tert-butyl hydrazinecarboxylate (6.6 g, 50 mmol) and dihydro-2H-pyran-3(4H)-one (5 g, 50 mmol) in MeOH (50 mL) was stirred at 15 C. for 2 hours. The mixture was concentrated to remove MeOH and the crude was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=1:1) to afford tert-butyl 2-(dihydro-2H-pyran-3(4H)-ylidene)hydrazine-1-carboxylate (10 g, 47 mmol, 93% yield).

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

Reference£º
Patent; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Marigo, Mauro; Kehler, Jan; Rasmussen, Lars Kyhn; (27 pag.)US2017/291901; (2017); A1;,
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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

Sodium carbonate (15 mg, 0.14 mmol) and tetrahydro-2H-pyran-4-carbonyl chloride (26 mg, 0.18 mmol) were added to mixture of 5-amino-1-(4-chlorobenzyl)-2-(methylthio)pyrimidin-6(1H)-one (33.2 mg, 0.118 mmol) and THF (0.5 mL) under ice-cooling, and stirred under ice-cooling for 2 hours. The reaction mixture was added to saturated sodium hydrogen carbonate aqueous solution, and extracted with ethyl acetate. The extract was washed by saturated saline, dried over anhydrous sodium sulfate, and then concentrated in vacuo to give 3-(4-chlorobenzyl)-2-methylthio-5-(tetrahydro-2H-pyran-4-ylcarbonylamino)pyrimidin-6(1H)-one (48 mg, yield: 100%) as pale yellow solid. 1H-NMR (delta ppm TMS/DMSO-d6): 1.54-1.70 (4H, m), 2.50 (3H, s), 2.83-2.92 (1H, m), 3.27-3.35 (2H, m), 3.84-3.91 (2H, m), 5.25 (2H, s), 7.27 (2H, d, J=7.8 Hz), 7.41 (2H, d, J=7.8 Hz), 8.70 (1H, s), 9.31 (1H, s).

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

Reference£º
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; TANAKA, Satoru; HIRAMATSU, Yoshiharu; NOZU, Azusa; NAKAMURA, Ken’ichioh; (260 pag.)US2016/24072; (2016); A1;,
Tetrahydropyran – Wikipedia
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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

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.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