Category: Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.

A. 2,2,6,6-Tetramethyl-tetrahydro-2H-pyran-4-ol, 10a (0297) (0298) A solution of 2,2,6,6-tetramethyloxan-4-one (190 mg, 1.22 mmol) and NaBH4 (93 mg, 2.5 mmol) in THF (4 mL) and methanol (2 mL) was stirred for 1 h at RT. The reaction was then quenched by the addition of 0.1 mL of water. The resulting mixture was concentrated. The residue obtained was purified by column chromatography on silica gel (EtOAc/petroleum ether (1:5-1:3 v/v)) to give the compound 10a. 1H-NMR (300 MHz, CDCl3) delta (ppm): 3.88-3.97 (m, 1H), 1.71-1.77 (m, 2H), 1.36-1.37 (m, 1H), 1.20-1.25 (m, 1H), 0.97-1.05 (m, 6H), 0.89-0.95 (m, 6H)., 1197-66-6

As the paragraph descriping shows that 1197-66-6 is playing an increasingly important role.

Reference£º
Patent; Janssen Pharmaceutica NV; Meegalla, Sanath; Huang, Hui; Player, Mark R.; (53 pag.)US2016/9662; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1172623-99-2, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Ruthenium chloride (45 mg) was added to a solution oftert-butyl[(2R,3S)-5-hydroxy-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate (15.0 g; Formula IX;Example 10) and acetic acid (15.0 mL) in acetonitrile (45.0 mL) and water (7.5 mL) at0C. Sodium bromate (4.0 g) was added slowly to the reaction mixture at 0C to 5C overS hours, and then the mixture was stirred for 16 hours at -5C to 5C. After completion ofthe reaction, IPA (15 mL) was added over 25 minutes at 0C to 5C, and then the mixture was stirred for 15 minutes. Water (180 mL) was slowly added to the reaction mixture, and then the mixture was stirred for 5 hours at 0C to 5C. The reaction mixture was filtered, and then dried under reduced pressure at 45C to 50C to obtain the title compound.Yield: 80%, 1172623-99-2

The synthetic route of 1172623-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; PANDYA, Bhargav; THAKUR, Mandeep; SURADKAR, Swapnil; ANGADI, Surender; (42 pag.)WO2017/81590; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1240390-36-6, tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1240390-36-6, Step 2 {(3R,4R)-4-[7-(5-Methyl-4,5-dihydro-pyridin-2-yl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester To a solution of 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (5-methyl-4,5-dihydro-pyridin-2-yl)-amide (0.071 g, 0.233 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.0756 g, 0.350 mmol) in dioxane (3 mL) was added diisopropylethylamine (0.122 mL, 0.699 mmol). The reaction mixture was heated at 120 C. overnight. The reaction mixture was cooled and then diluted with dichloromethane, washed with aqueous sodium carbonate, then brine, dried over anhydrous Na2SO4, filtered and concentrated. Purification by chromatography (silica, 40 g, 0 to 50% ethyl acetate in hexanes) gave {(3R,4R)-4-[7-(5-methyl-4,5-dihydro-pyridin-2-yl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (0.047 g, 0.097 mmol, 41.6%) as a yellow solid. LCMS m/z [M+H]=485.

As the paragraph descriping shows that 1240390-36-6 is playing an increasingly important role.

Reference£º
Patent; Hoffmann-La Roche Inc.; Chen, Shaoqing; Hermann, Johannes Cornelius; Le, Nam T.; Lucas, Matthew C.; Padilla, Fernando; US2013/178460; (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.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

To a mixed solution of 62 (7.25 g, 32.5 mmol) and L12CUCI4 (16.2 mL, 0.1 M solution in THF, 1.62 mmol, 5 mol %) in THF (50 mL) at 0C was slowly added Grignard reagent ((cyclobutylmethyl)magnesium bromide) that5 was made from (bromomethyl)cyclobutane (9.69 g, 65.0 mmol) and grinded magnesium turnings (3.16 g, 130 mmol) in Et20 (50 mL). After the addition completed, stirred at 0C for 30 min and then at RT for 18 hr. The reaction was quenched by NH4Cl at 0C and stirred at RT for 20 min. Then the mixture was treated with hexanes and water. Organic phase was washed by brine, dried over Na2S04, and concentrated to give 63 (6.9 g, 100%) as a colorless oil. ‘H NMR (400 MHz, Chloroform-ri) d 4.57 (dd, J= 4.5, 2.7 Hz, 1H), 3.87 (ddd, .7= 11.1, 7.4, 3.4 Hz, 1H), 3.72 (dt, J = 9.6, 6.9 Hz, 1H), 3.56 – 3.45 (m, 1H), 3.37 (dt, J= 9.6, 6.7 Hz, 1H), 2.24 (dq, J= 15.5, 7.8 Hz, 1H), 2.10 – 1.93 (m,3H), 1.91 – 1.64 (m, 4H), 1.62 – 1.45 (m, 7H), 1.39 (q, J= 7.4 Hz, 2H), 1.25 (tdd, J= 10.0, 7.2, 3.9 Hz, 2H). 13C NMR (101 MHz, Chloroform-ri) d 98.78, 67.65, 62.28,36.79, 36.06, 30.73, 29.70, 28.32 (2C), 25.46, 23.77, 19.66, 18.43.

33821-94-2, 33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; TSRL, INC.; LIPKA, Elke D.; SIMON, Eric; WHITE, Andy, D.; HUTCHINGS, Kim, M.; GAN, Xinmin; (0 pag.)WO2020/6050; (2020); A1;,
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,125995-03-1

An authentic sample of Lactone (530mg) was dissolved in anhydrous DMF (5ML), followed by imidazole (174mg), then TBDMS chloride (371 mg). The mixture was stirred at room temperature. After 6 hours, the reaction was worked up by addition of ET20 (30ML) and water (30ML). The separated organic phase was further washed with water (2 x 20MOI), dried, and concentrated in vacuo to afford silylated lactone as a white powder (470mg, 73%). The silylated lactone (233mg) was dissolved in anhydrous dichloromethane (5ML), then COOLED TO-78C under Nitrogen. DIBAL (0. 31 ml, 1 M in toluene) was added dropwise and the mixture stirred for 10 minutes AT-78C. The mixture was then quenched by addition of 1 ml of 10% aqueous Rochelle’s salt and allowed to warm to room temperature. After addition of further DICHLOROMETHANE (10ML) and water (10MOI), the phases were separated and the organic phase dried and concentrated in vacuo. The residual oil was purified by column chromatography (50% ET20 in hexane). FTIR : 1668 CM~ (amide). Stretch at 1735CM (Lactone) no longer present. The silylated lactol (100mg) was dissolved in anhydrous THF. HF. pyridine was added (0. 1ML) at 0C and allowed to warm to room temperature. The mass was quenched with ether/and sodium bicarbonate solution. The phases separated and the aqueous phase back extracted with ether. The organic phases were combined, dried and evaporated to produce and oil (75mg). M/z 542,524, 506;’H nmr CDC13 1.3 (d, 6H), 1.6- 1.9 (m, 6H), 3.45 (2H), 3.6 (m, 2H), 3.8 (m, 1H), 5.0 (m, 1H), 6.8 (br. s 1H), 7.1 (m, 14H); 3C nmr CDCI3 91.6ppm (Lactol C); FTIR : 1652CM (Amide)

As the paragraph descriping shows that 125995-03-1 is playing an increasingly important role.

Reference£º
Patent; AVECIA LIMITED; WO2005/12246; (2005); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

624734-17-4, 3-Methoxydihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

624734-17-4, General procedure: Toa solution of ((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone (119 mg, 0.33 mmol, 1 eq) in DCM at rtwas added acetic acid (0.01 mL, 0.17 mmol, 0.5 eq),3-methoxytetrahydro-4H-pyran-4-one (131 mg, 1.0 mmol, 3 eq) and sodiumtriacetoxyborohydride (355 mg, 1.67 mmol, 5 eq). After stirring overnight, saturated NaHCO3was added, the solution extracted with DCM, the organics combined, dried overMgSO4, and concentrated.Purification by chromatography (12 g) eluting with 4 to 8% methanol/DCMwith ammonia afforded compound 2a ((3aS,5S,6aR)-5-((3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H-cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone(83 mg, 50%). 1H NMR (CHLOROFORM-d)d: 8.72 (br. s., 1H), 7.70 (br. s., 1H), 4.98 -5.14 (m, 1H), 4.70 – 4.89 (m, 2H),3.80 – 4.18 (m, 5H), 3.25 – 3.75 (m, 8H), 3.07 – 3.24 (m, 2H), 2.53 – 2.89 (m,1H), 2.01 – 2.48 (m, 4H), 1.39 – 1.88 (m, 5H).ESI-MS (m/z): Calculated for C23H30F3N3O4:470.2 (M+1); found: 470.2.

As the paragraph descriping shows that 624734-17-4 is playing an increasingly important role.

Reference£º
Article; Winters, Michael P.; Teleha, Christopher A.; Kang, Fu-An; McComsey, David; O’Neill, John C.; Hou, Cuifen; Kirchner, Thomas; Wang, Ping; Johnson, Dana; Sui, Zhihua; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2137 – 2140;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A stirred mixture of (S)-(+)-prolinol (0.4 14 g, 3.99 mmol), NiC12-glyme (0.449 g, 1.99 mmol), phenyl boronic acid (3.04 g, 24.98 mmol) and KHMDS (6.6 g, 33.3 mmol) was submitted to few cycles of vacuumlargon flow. i-PrOH (40 mL) was added and the resulting mixture was stirred at r.t. for 10 mm, then 4-chlorotetrahydropyran (1.75 mL, 16.6 mmol) wasadded dropwise. The resulting yellowish mixture was heated at 65 C for 50 h, then cooled at r.t., diluted with EtOAc (200 mL) and washed with 10% HC1 solution (30 mL), sat. NaHCO3 solution (30 mL x 2) and brine (40 mL). The organic layer was dried over Na2504, filtered and concentrated to dryness to afford a solid crude (2.5 g). Purification by typical silica gel flash chromatography using a Teledyne ISCO apparatus (Cy/TBME from 100:0 to 80:20) afforded thepure title compound (1.29 g, 48%), as a liquid. R= 2.36 mm. ?H NMR (CDC13): oe 7.40-7.28 (m,2H), 7.24-7.19 (m, 3H), 4.20-4.07 (m, 2H), 3.57 (td, 2H, J= 11.5, 2.5 Hz), 2.80 (tt, 1H, J= 11.5,4.2 Hz), 1.94-1.75 (m, 4H)., 1768-64-5

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

Reference£º
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; PIOMELLI, Daniele; BANDIERA, Tiziano; BERTOZZI, Fabio; NUZZI, Andrea; FIASELLA, Annalisa; PONZANO, Stefano; PAGLIUCA, Chiara; REGGIANI, Angelo Mario; WO2014/144836; (2014); A2;,
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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

2c (5.5g, 34.97mmol) and ammonium acetate (8.1g, 104.9mmol) in methanol (100mL) were stirred at room temperature overnight. The mixture was concentrated in vacuo, and diluted with water (50mL) and extracted with DCM (50mL¡Á3). The separated organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting crude methyl 4-amino-5,6-dihydro-2H-pyran-3-carboxylate 3c was then dissolved in acetonitrile (50mL), and 2,2,2-trichloroacetyl isocyanate (7.2g, 38.46mmol) was added. The resulting mixture was stirred for 30min, and the precipitated solids were collected and dissolved in a solution of ammonia in methanol (10mL, 7N). Then the resulting mixture was heated at 70C for 1h. The reaction was cooled down and the precipitated solids were collected and dried to afford the diol (4c) (3.8g, yield 65%, purity 97%) as a white solid. MS (ESI) m/z 169.2 [M+H]+., 127956-11-0

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

Reference£º
Article; Wang, Xueyuan; Bai, Enhe; Zhou, Hui; Sha, Sijia; Miao, Hang; Qin, Yanru; Liu, Zhaogang; Wang, Jia; Zhang, Haoyang; Lei, Meng; Liu, Jia; Hai, Ou; Zhu, Yongqiang; Bioorganic and Medicinal Chemistry; vol. 27; 3; (2019); p. 533 – 544;,
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.

Preparation 1; Methanesulfonic acid tetrahydropyran-4-ylmethyl ester; A solution of 90 g (774.8 mmol) of tetrahydropyran-4 -methanol and 129.6 mL (929.76 mmol, 1.2 eq.) of triethylamine in 775 mL of anhydrous DCM was cooled to 00C with in an ice bath. Methanesulfonyl chloride (66.2 mL, 852.28 mmol, 1.1 eq.) of was then added dropwise over 60 minutes while maintaining the temperature around O0C. The reaction mixture was stirred for 30 minutes at O0C and quenched with a saturated solution of sodium bicarbonate (800 mL) . The aqueous layer was extracted with DCM (800 mL) . The combined organic layers were washed with water (2 x 800 mL) , brine (800 mL) and dried over sodium sulfate. After filtration and concentration in vacuo, a yellowish solid (146.1 g, 97%) was obtained corresponding to the methanesulfonic acid tetrahydropyran-4-ylmethyl ester.IH NMR (400 MHz, DMSOd6): delta [ppm] 4.02 (d, 2H), 3.82 (m, 2H), 3.27 (t x d, 2H), 3.14 (s, 3H), 1.89 (m, IH), 1.55 (m, 2H), 1.21(q x d, 2H) .; Preparation 13; Methanesulfonic acid tetrahydropyran-4-ylmethyl ester; A solution of 90 g (774.8 mmol) of tetrahydropyran-4 -methanol and 129.6 mL (929.76 mmol, 1.2 eq.) of t?ethylamine m 775 mL of anhydrous DCM was cooled to 00C m an ice bath. Methanesulfonyl chloride (66.2 mL, 852.28 mmol, 1.1 eq.) was then added dropwise over 60 minutes while maintaining the temperature around 00C. The reaction mixture was stirred for 30 minutes at 00C and quenched with a saturated solution of sodium bicarbonate (800 mL) . The aqueous layer was extracted with DCM (800 mL) . The combined organic layers were washed with water (2 x 800 mL) , brine (800 mL) and dried over sodium sulfate. After filtration and concentration m vacuo, a yellowish solid (146.1 g, 97%) was obtained corresponding to the methanesulfonic acid tetrahydropyran-4-ylmethyl ester .IH NMR (400 MHz, DMSO-O6): delta [ppm] 4.02 (d, 2H), 3.82 (m, 2H), 3.27 (t x d, 2H), 3.14 (s, 3H), 1.89 (m, IH), 1.55 (m, 2H), 1.21 (q x d, 2H) ., 14774-37-9

14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; VIROCHEM PHARMA INC.; WO2007/143847; (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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

(u) 2-(m,p-dimethoxyphenyl)-ethyl, m.p. 188-191; The amine starting material for compound (e), 2-(tetrahydropyran-4-yl)-ethylamine, can be prepared from tetrahydropyran-4-one e.g. by Wittig condensation with diethyl cyanomethyl phosphonate followed by hydrogenation and reduction with lithium aluminum hydride., 29943-42-8

As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; Ciba-Geigy Corporation; US4977144; (1990); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics