Day: November 16, 2020

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

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

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

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

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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

A suspension solution of152F (30 mg, 0.089 mmol), 4-(bromomethyl)tetrahydropyran (16.73 mg, 0.093 mmol)and C52CO3 (43.5 mg, 0.133 mmol) in DMF (1 mL) was heated to 120 C for 20 mm and 140 C for 1 h under microwave conditions. The reaction mixture was concentrated invacuo. Water (2 mL) was added and stirred for 5 minutes. The solid was collected as the crude product which was purified by column chromatography on the Isco system to yield152G (25 mg, 65% yield). MS(ESI) m/z 435.2 (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; BRISTOL-MYERS SQUIBB COMPANY; HART, Amy C.; PITTS, William J.; MASTALERZ, Harold; GUO, Junqing; BROWN, Gregory D.; (148 pag.)WO2016/100166; (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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

Example 4 N-(4-Ethoxy-6-{4-oxo-2-[(tetrahydro-pyran-4-ylmethyl-amino)-4H-thiazol-5-ylidenemethyl}-quinolin-2-yl]-acetamide a) Preparation of c-(tetrahydro-pyran-4-yl)-methylammonium acetate A cold (ice water bath) solution of tetrahydro-4H-pyran-4-one (7.5 g, 75 mmol) and tosylmethylisocyanide (16.05 g, 82.4 mmol) in DME (125 ml) was treated with a suspension of potassium t-butoxide (16.8 g, 150 mmoles) in t-butyl alcohol (250 ml). The reaction mixture was stirred at room temperature for 31/2 hours, and then diluted with ether (250 ml). The mixture was successively washed with water and brine, then dried over sodium sulfate, filtered, and concentrated. The crude product was purified by short path distillation under high vacuum to give the nitrile as colorless oil (2.98 g). This material was dissolved in 1M borane/tetrahydrofuran (THF) (134 ml, 134 mmol) and stirred at rt overnight. Excess borane was quenched by adding methanol (rt, 1 h), and the mixture was concentrated to dryness. The residue was dissolved in 4N HCl/dioxane, stirred at rt for 1 h and then concentrated under reduced pressure. The solid residue was triturated with ether and collected by suction filtration. A suspension of this material (1.81 g, 11.9 mmol) in THF (30 ml) was treated with 1N NaOH (11.9 ml, 11.9 mmol) at rt for ? h. The THF was removed by distillation and the aqueous solution was saturated with NaCl then extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was treated with acetic acid (0.68 ml, 11.9 mmol) to provide, after drying in a vacuum oven, c-(tetrahydro-pyran-4-yl)-methylammonium acetate (1.71 g).

29943-42-8, 29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Chen, Li; Chen, Shaoqing; Michoud, Christophe; US2006/63804; (2006); 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.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

Under nitrogen atmosphere, magnesium (6.05 g, 249 mmol) was suspended in THF (30 ml). A catalytic amount of iodine and dibromoethane (0.4 ml) were added. The mixture was heated to 60C and 4-chlorotetrahydro-2H-pyran (5 g, 41.5 mmol) in THF (5 ml) was added dropwise. The mixture was stirred at 60C for 2.5 h. The mixture was cooled to 0C and N-[[5-benzyloxy-l-[2- [tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-2-pyridyl]methylene]-2-methyl-propane-2- sulfinamide (Intermediate 5, 6.78 g, 13.82 mmol) in THF (20 ml) was added. The resulting mixture was stirred at rt for 45 min. The reaction was quenched with ammonium chloride solution and extracted with EtOAc (2x). The combined organic layers were washed with brine, dried with sodium sulfate and concentrated to afford the title intermediate as an orange gum (8.7 g). Purification by chromatography (Si02, 10% MeOH in DCM) gave the title intermediate as an orange oil (7.3 g, 56 %). MS, ES+ m/z, 577 (M+H)+.

1768-64-5, 1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; LIEBER INSTITUTE FOR BRAIN DEVELOPMENT; BARROW, James; ERNST, Glen; SWINNEN, Dominique; MONTEL, Florian; DEFAYS, Sabine; (224 pag.)WO2017/91818; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics