Category: Tetrahydropyrans

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.

General procedure: Sodium hydride (60% suspension in mineral oil, 31 mg, 0,76 mmol) is added to asolution of 36a (109 mg, 91 % content, 0,63 mmol) in DMF (1 mL) at 0C. After 20mi 2-(trimethylsilyl)ethoxymethyl chloride (157 p1, 0,88 mmol) is added dropwise tothe reaction mixture. After stirring for 1 h at rt, the reaction is diluted with EtOAc,washed with NaHCO3 satured solution and brine. The organic layer is separated and dried with a Phase separator cartridge and evaporated under vacuum to give a residue that is purified by flash chromatography (eluent 0-10% EtOAc/cyclohexane) to furnish the title compound (182 mg).UPLC-MS (Method 2): Rt = 1 .61MS (ESI pos): mlz = 288 (M+H)+

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; CUI, Yunhai; DOODS, Henri; FERRARA, Marco; JUST, Stefan; KUELZER, Raimund; LINGARD, Iain; MAZZAFERRO, Rocco; RUDOLF, Klaus; WO2014/184275; (2014); 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

A mixture of tetrahydropyran-3-one (0.25g) and 2-amino-2-(4-bromophenyl)acetamide (D1 ) (0.572g) and H-Y Zeolites (0.57g) in methanol (25ml) was refluxed under argon overnight. The mixture was filtered through Kieselguhr and the solvent was removed to give crude title compound as a yellow solid which was used without purification (712mg). Mass spectrum Found 311/3 (MH+)., 23462-75-1

The synthetic route of 23462-75-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2009/34061; (2009); 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.19752-84-2,Tetrahydro-2H-pyran-3-ol,as a common compound, the synthetic route is as follows.

Preparation 27; 4-Bromo-2-((tetrahydro-2H-pyran-3-yl)oxy)pyridine To a solution of tetrahydro-2H-pyran-3-ol (0.10 g, 0.97 mmol) in THF (2.5 mL) was added sodium hydride (60% dispersion in mineral oil, 0.065 g, 1.6 mmol) and stirred at ambient temperature for about 2 h. To the reaction mixture was added 4-bromo-2-fluoropyridine (0.144 g, 0.816 mmol) in THF (2.5 mL). After about 16 h, water (5 mL) and EtOAc (10 mL) were added. The organic layer was separated and the aqueous layer was back extracted with EtOAc (10 mL). The combined organic layers were dried over MgS04, filtered and concentrated under reduced pressure. The material was purified via flash chromatography on silica gel (0-50% EtOAc/heptane). The appropriate fractions were collected and concentrated under reduced pressure to provide the title product (0.1 17 g, 55%); LC/MS (Table A, Method i) = 1.33 min.; MS m/z: 258 and 260 (M+H) ., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBVIE INC.; ARGIRIADI, Maria; BREINLINGER, Eric; DIETRICH, Justin, D.; FRIEDMAN, Michael; IHLE, David; MORYTKO, Michael; MULLEN, Kelly; OSUMA, Augustine; LO SCHIAVO, Gloria, Y.; WILSON, Noel, S.; (303 pag.)WO2016/168633; (2016); A1;,
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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.

2. A solution of 4-chlorotetrahydro-2H-pyran (1 g, 8.29 mmol) in anhydrous THF (8 mL) was added dropwise to a mixture of Mg (401 mg, 16.5 mmol) and I2 (105 mg, 0.414 mmol) in anhydrous THF 2 mL) under N2 at 60oC. The mixture was stirred at 60oC for 10 min. The temperature rose to 66oC. The reaction mixture was stirred for additional 30 min, cooled to room temperature which was used directly as a solution of (tetrahydro-2H-pyran-4-yl)magnesium chloride (0.83 M in THF)., 1768-64-5

As the paragraph descriping shows that 1768-64-5 is playing an increasingly important role.

Reference£º
Patent; SAGE THERAPEUTICS, INC.; SALITURO, Francesco, G.; ROBICHAUD, Albert, J.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; GRIFFIN, Andrew; LA, Daniel; (299 pag.)WO2018/75698; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

KHMDS (1M in THF) (39.0 mL, 39.0 mmol) was added to THF (150 mL) at -78C under nitrogen. A solution of 1-(tetrahydro-2H-pyran-4-yl)ethanone (5 g, 39.0 mmol) in THF (20 mL) was added and the mixture was stirred at -78C under nitrogen for 1 .5h, giving a pale yellow solution. A solution of N-(5- chloropyridin-2-yl)-1 ,1 ,1 -trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide (15.32 g, 39.0 mmol) in THF (25 mL) was added over 20 minutes and the resulting orange, then colourless mixture was allowed to warm slowly to room temperature and stirred overnight. The reaction was quenched with NaHCO3 and the crude product extracted with MTBE (300 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under vacuum. The residue was dissolved in a small amount of 10% EtOAc:lsohexane and loaded on a 40g column. The crude product was purified by chromatography (Si02, 40 g column, 0-10% EtOAc/isohexane). Fractions containing product were combined, filtered, washing with 10% EtOAc:lsohexane, then concentrated. A solid formed in the residue, which was then taken up in 10% EtOAc:lsohexane, filtered through cotton wool. The filtrate was then loaded on a 40g column and the crude product was purified by chromatography (Si02, 40 g column, 0-10% EtOAc/isohexane) to afford 1 -(tetrahydro-2H-pyran-4-yl)vinyl trifluoromethanesu Ifonate (6.17 g, 20.15 mmol, 51.7% yield) as a colourless oil. 1H NMR (CDCI3) O: 5.14 (dd, 1H), 4.94 (dd, 1H), 4.06 – 3.98 (m, 2H), 3.41 (td, 2H), 2.54 -2.41 (m, 1 H), 1.89 – 1.79 (m, 2H), 1.66 – 1.50 (m, 2H)., 137052-08-5

The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; HOWARD, Steven; CONS, Benjamin, David; ST. DENIS, Jeffrey, David; GRIFFITHS-JONES, Charlotte, Mary; HISCOCK, Steven, Douglas; HOLVEY, Rhian, Sara; BURNS, Alan, Richard; COUSIN, David; DEXTER, Hannah, Louise; PARRA, Guillaume, Francois; WATTS, John, Paul; JEWELL, Robert; STOCKWELL, Jennifer, Ann; HIRST, Kim, Louise; LEMASSON, Isabelle, Anne; NASH, David, John; OSBORNE, James, Daniel; PRIEDE, Jonas, Calleja; RICHARDS, Nicholas, Paul; DUMAS, Aaron, Michael; BISHOP, Brian, Christopher; PARRY-JONES, David; SCOTT, Jeremy, Peter; SHAUNMUGHAM, Meenakshi, Sundaram; MULLENS, Peter, Richard; LATHBURY, David, Charles; DIXON, Darren, James; GAUNT, Matthew, James; (291 pag.)WO2018/178691; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

EXAMPLE 1 Synthesis of 3-hydrazinocarbonylmethyl-5-methyl-hexanoic acid (III)A 100 ml three-necked round-bottom flask, under nitrogen atmosphere, is added with 98% hydrazine hydrate (19.5 g, 0.382 mols), sodium hydroxide (12.4 g, 0.309 mol) in water (150 ml) and the solution is cooled to a temperature of -5 C. A solution of 3-isobutyl-glutaric anhydride (50.0 g, 0.294 mol) in toluene (200 ml) is dropped therein in about 1-2 h, keeping the temperature below 0-5 C. The mixture is reacted for about 1 h, then the phases are separated, the aqueous phase is concentrated to small volume, thereby obtaining a white solid which is taken up into isopropanol (100 ml) and filtered. The solid is dried under vacuum at a temperature of 30-35 C. for 16-18 hours. 56.7 g of product are obtained, in an 86% yield.1H-NMR (300 MHz, D2O, 28 C.): delta 2.20-1.90 (m, 5H); 1.50 (m, 1H); 1.05 (m, 2H); 0.75 (d, 6H)., 185815-59-2

185815-59-2 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione 11480690, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Dipharma Francis S.r.l.; US2009/143615; (2009); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

4295-99-2, 4-Cyanotetrahydro-4H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4295-99-2

Example 44 (Synthesis of 4-aminomethyltetrahydropyran hydrochloride) In an autoclave made of stainless equipped with a stirring device, a thermometer and a pressure gauge and having an inner volume of 25L were charged 1685.8 g (containing 15.2 mol of 4-cyanotetrahydropyran) of 65.9% by weight 4-cyanotetrahydropyran-toluene solution, 8.8 kg of 5.86% by weight ammonia-methanol solution, 337.2 g (2.86 mmol in terms of a nickel atom) of developed Raney nickel (available from Nikki Chemical Co., Ltd.; sponge nickel N154D) and 2.1 L of methanol, and the mixture was reacted under hydrogen atmosphere (0.51 to 0.61 MPa) at 50 to 60C for 7 hours under stirring. After completion of the reaction, insoluble materials were filtered, the filtrated material was washed with 2.0 L of methanol, and the filtrate and the washed solution were combined and concentrated under reduced pressure. To a reaction vessel made of glass equipped with a stirring device and a thermometer and having an inner volume of 3 L were charged said concentrate and 833 ml of tetraethylenepentamine, the mixture was stirred at 105 to 115C for 2 hours. After completion of the stirring, said solution was distilled under reduced pressure (70 to 80C, 1.73 to 4.67 kPa) to obtain 1430.2 g of the distilled solution containing 4-aminomethyltetrahydropyran. To a reaction vessel made of glass equipped with a stirring device, a thermometer and a dropping funnel and having an inner volume of 20 L were charged 8.3 L of n-butanol and 1232 ml (15.0 mol) of 37% by weight hydrochloric acid, and in a salt-ice bath, said distulled solution was gradually added dropwise to the mixture while maintaining a temperature of the mixture to 0C or therearound, and after completion of dropwise addition, the mixture was stirred at room temperature for 30 minutes. An operation that the resulting solution was concentrated under reduced pressure, and 5.0 L of n-butanol was added to the concentrate and further concentrated was repeated twice. Then, in a salt-ice bath, when the concentrate was stirred for 50 minutes, a solid was precipitated and filtered. The filtered material was washed with 1.7 L of toluene, and then, it was dried under reduced pressure at 60C to give 1692.9 g (Isolation yield: 73.6%) of 4-aminomethyltetrahydropyran hydrochloride as white crystals. Physical properties of 4-aminomethyltetrahydropyran hydrochloride are as follows. Melting point; 190 to 193C 1H-NMR (DMSO-d6, delta (ppm)); 1.13 to 1.26 (2H, m), 1.63 to 1.68 (2H, m), 1.78 to 1.92 (1H, m), 2.67 (2H, d, J=7.1Hz), 3.22 to 3.30 (2H, m), 3.82 to 3.87 (2H, m), 8.21 (3H, brs) CI-MS (m/e); 116 (M+1-HCl), 99

As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

Reference£º
Patent; Ube Industries, Ltd.; EP1671937; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

127956-11-0, Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 10: 2-Chloromethyl-3, 5, 7, 8-tetrahydro-pyrano[4, 3-d]pyrimidin-4-one A mixture of crude 4-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester (1780 g, 1 1 mol) and NEt3 (830 g, 8.2 mol) in MeOH (3560 mL) was cooled to 0C under N2. A solution of 2-chloro-acetamidine (567 g, 4.4 mol) in 890 mL of MeOH was added dropwise over 50 minutes. The reaction mixture was stirred at 0C for 30 minutes and then at about 20C for 16 hours. LCMS at 215nm and TLC (DCM:MeOH=10:1 ) analysis showed that most of 4-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester was consumed. The mixture was then filtered and concentrated to give black oil, which was subsequently purified by flash column chromatography on silica gel and eluted with DCM to give yellow solid/oil mixture, which was further triturated with MTBE (-1200 mL) and H20: CHsCN: EA=1 :1 :2 (-600 mL) to give the title compound as a white solid (318 g). MS m/z 201.2 (M+H). CHN analysis: calculated (results). C 47.89 (47.95), H 4.52 (4.401 ), N 13.96 (13.76).

127956-11-0, 127956-11-0 Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate 14666555, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; CHEN, Zhuoliang; CHEUNG, Atwood, Kim; CHIN, Donovan, Noel; FAN, Jianmei; MILLER-MOSLIN, Karen, Marie; SHULTZ, Michael, David; SMITH, Troy, D.; TOMLINSON, Ronald, Charles; TOURE, Bakary-Barry; VISSER, Michael, Scott; WO2013/12723; (2013); A1;,
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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, This compound was prepared following a procedure adopted in similar cases.20 beta-d-Glucose pentaacetate (3.83 g, 9.82 mmol) and BF3¡¤Et2O (1.24 mL, 9.82 mmol), previously dissolved in 15 mL of dry dichloromethane, were added under a nitrogen atmosphere to a solution of (4-iodo-phenoxy)-trimethylsilane 17 (2.39 g, 8.18 mmol) in 15 mL of CH2Cl2 kept at room temperature. After 12 h the reaction mixture was washed with saturated aqueous bicarbonate 50 mL¡Á3 and brine 50 mL¡Á2 and dried over anhydrous Na2SO4. Evaporation of the solvent at reduced pressure gave the crude product that was purified by column chromatography over silica gel, using a mixture of petroleum ether/ethyl acetate 6:4 as eluent obtaining 10a as a white solid (3.65 g, 81% yield). (Found: C, 43.61, H, 4.20. C20H23IO10 requires C, 43.65, H, 4.21); Rf (petroleum ether/ethyl acetate 6:4) 0.49; mp 144-145 C (methanol). deltaH (CDCl3, 400 MHz): 1.99 (3H, s, CH3), 2.00 (3H, s, CH3), 2.01 (3H, s, CH3), 2.03 (3H, s, CH3), 3.78-3.86 (1H, m, CH), 4.12 (1H, dd, J 12.3, 2.4 Hz, CH2), 4.24 (1H, dd, J 12.3, 5.4 Hz, CH2), 5.00 (1H, d, J 7.6 Hz, anomeric CH), 5.11 (1H, t, J 9.6 Hz, CH), 5.18-5.29 (2H, m, 2CH), 6.70-6.75 (2H, app d, J 9.0 Hz, Ph), 7.52-7.57 (2H, app d, J 9.0 Hz, Ph). deltaC (CDCl3, 100 MHz) 20.5 (CH3), 20.6 (2CH3), 20.8 (CH3), 61.8 (CH2), 68.1 (CH, glucose ring), 71.0 (CH, glucose ring), 72.0 (CH, glucose ring), 72.5 (CH, glucose ring), 86.2 (C-I, Ph), 98.9 (anomeric CH), 119.2 (C, Ph), 138.4 (C, Ph), 156.6 (C, Ph), 169.2 (CO), 169.3 (CO), 170.2 (CO), 170.5 (CO). numax/cm-1 (KBr): 818, 1041, 1224 (s, C-O-C), 1432, 1485, 1587, 1750 (s, CO), 2961.

83-87-4 (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 10293747, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Hassan Omar, Omar; Babudri, Francesco; Farinola, Gianluca M.; Naso, Francesco; Operamolla, Alessandra; Pedone, Adriana; Tetrahedron; vol. 67; 2; (2011); p. 486 – 494;,
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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 mixture of (tert-butoxycarbonyl)-L-valine (3.64 g, 16.75 mmol), 4-(bromomethyl)tetrahydro-2H- pyran (3.00 g, 16.75 mmol) and NaHCO3 (2.81 g, 33.50 mmol) in DMF (30 mL) was stirred at 70 C for 12 hours under N2 atmosphere. The reaction mixture was diluted with H20 (100 mL) and extracted with MTBE (50 mL x 2). The combined organic layers were washed with brine (20 mL x 2), dried overNa2SO4, filtered and concentrated under reduced pressure to give (tetrahydro-2H-pyran-4-yl)methyl(tert-butoxycarbonyl)-L-valinate (5 g, yield 94.63%, pale yellow oil) which was used into the next stepwithout further purification. 1H NMR (400 MHz, CDCI3) O 5.01 (d, J = 8.4 Hz, 1H), 4.22 (dd, J = 8.8 Hz,4.8 Hz, 1H), 4.00-3.97 (m, 4H), 3.40 (t, J= 11.2 Hz, 2H), 2.16-2.11 (m, 1H), 1.96-1.90 (m, 1H), 1.63 (d, J= 13.2 Hz, 2H), 1.45 (s, 9H), 0.97 (d, J 6.4 Hz, 3H), 0.90 (d, J 7.2 Hz, 3H)., 125552-89-8

As the paragraph descriping shows that 125552-89-8 is playing an increasingly important role.

Reference£º
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; CARTER, David Scott; HALLADAY, Jason S.; JACOBS, Robert T.; LIU, Yang; PLATTNER, Jacob J.; ZHANG, Yong-Kang; WITTY, Michael John; (149 pag.)WO2017/195069; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics