Tag: 19752-84-2

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Oxidation of alcohol 49 (2.12 g, 20.8 mmol) with DMP (9.91 g, 23.3 mmol) in accordance with Method Y provides the pyranone 50 (1.78 g): 1H NMR (250 MHz, CDCl3, deltaH) 4.03 (s, 2H), 3.86 (app t, 2H), 2.54 (app t, 2H), 2.12 (m, 2H).; Method Y[0277] To a suspension of the 3-pyranol (1 equiv) and 4 A molecular sieves (2 g/g 3- pyranol) in DCM (5 mL/mmol) is added DMP (1 equiv) portionwise over 20 min. Reaction progress is monitored by TLC. Additional DMP (0.2 equiv) is added as required. After 1 h, the reaction mixture is partitioned between DCM and 2 M K2CO3. The organic phase is separated and the aqueous extracted with DCM (3 x). The combined organic phases are washed with brine, dried (MgSO4), filtered, and coned in vacuo. Column chromatography (silica gel, 1:2 EtOAc in heptanes) provides the 3-pyranones., 19752-84-2

As the paragraph descriping shows that 19752-84-2 is playing an increasingly important role.

Reference£º
Patent; PANACOS PHARMACEUTICALS, INC.; NITZ, Theodore, J.; SALZWEDEL, Karl; FINNEGAN, Catherine; BRUNTON, Shirley; FLANAGAN, Stuart; MONTALBETTI, Christian; COULTER, Thomas, Stephen; WO2009/85256; (2009); A1;,
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19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

STEP 2. DIHYDRO-2H-PYRAN-3(4H)-ONE To a stirred mixture of pyridinium chlorochromate (11.02 g, 51.1 mmol) and 3 A molecular sieves (10.0 g) in DCM (100 mL) was added a solution of tetrahydro-2H-pyran-3-ol (3.48 g, 34.1 mmol) in DCM (100 mL). The reaction mixture was refluxed for 3 h before being cooled to room temperature and partially concentrated in vacuo. The mixture was then diluted with EtOAc and filtered through Celite. The filtrate was concentrated in vacuo and purified by silica gel chromatography to give dihydro-2H-pyran-3(4H)-one., 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; AMGEN INC.; US2010/160280; (2010); 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.

To a solution of DIAD (2.0 equiv.) and triphenylphosphine (2.0 equiv.) in THF (0.24 M) was added tetrahydro-2H-pyran-3-ol (1.2 equiv.). The mixture was stirred for 10 min. methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropicolinate (1.0 equiv.) was added. The mixture was stirred at ambient temperature overnight. Additional triphenylphosphine (2.0 equiv.) and DIAD (2.0 equiv.) were added, and the mixture was stirred overnight. The mixture was concentrated and purified by flash chromatography over silica gel (heptanes:ethyl acetate gradient) to give methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-3-yl)oxy)phenyl)-5-fluoropicolinate in 39% yield. Purification was completed via chiral HPLC (EtOH/heptane)=15/85, 20 mL/min, AD column) to yield (S)-methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-3-yl)oxy)phenyl)-5-fluoropicolinate (18% yield, 99% ee) and (R)-methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-3-yl)oxy)phenyl)-5-fluoropicolinate (18% yield, 99% ee). LC/MS=368.2 (MH+), Rt=0.92 min. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.65 (ddd, J=12.81, 8.51, 4.11 Hz, 1H), 1.78-1.97 (m, 2H), 2.06-2.16 (m, 1H), 3.57-3.67 (m, 2H), 3.72-3.80 (m, 1H), 3.95 (dd, J=11.54, 2.15 Hz, 1H), 3.99-4.01 (m, 3H), 4.32 (dt, J=6.95, 3.37 Hz, 1H), 6.54-6.62 (m, 2H), 7.59-7.67 (m, 1H), 8.19-8.28 (m, 1H)., 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; Burger, Matthew; Ding, Yu; Han, Wooseok; Nishiguchi, Gisele; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225061; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tetrahydro-2H-pyran-3-ol (2.0 g) in DCM (100 mL) was added TEA(4.0 g) and methanesulfonyl chloride (2.7 g) at 0C under a nitrogen atmosphere. The resultingmixture was stirred at this temperature for 30 mins, and then quenched with aq. NaHCO3 solution. The mixture was extracted with DCM (2×50 mL). The combined organic phases were washed, dried and concentrated to afford tetrahydro-2H-pyran-3-yl methanesulfonate (3.2 g) as a brown oil.

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

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHEN, Weichun; IGBOKO, Ebere F; LIN, Xichen; LU, Hongfu; REN, Feng; WREN, Paul Bryan; XU, Zhongmiao; YANG, Ting; ZHU, Lingdong; WO2015/181186; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Protocol A. To a suspension of the corresponding carboxylic acid 7-9 (0.25 mmol) in DMF (1 mL) were added DIEA (0.75 mmol, 3.0 eq), TBTU (0.325 mmol, 1.3 eq), HOBt (0.075 mmol, 0.3 eq) and the reaction mixture was stirred at rt for 5 min, followed by addition of the corresponding alcohol (1.1-5.0 eq). The reaction mixture was stirred at rt for 1-16h, then diluted with EtOAc (100 mL), washed with aqueous saturated sodium carbonate solution (50 mL), 0.1M HCl (50 mL), water (50 mL) and brine (50 mL). The organic phase was then dried over MgSO4 and concentrated under reduced pressure to afford the desired ester. Protocol B. To a solution of the corresponding carboxylic acid 7-9 (1.0 eq) in DCM were successively added DCC (1.0 eq), HOBt (1.0 eq) and DIEA (3.0 eq). The solution was stirred at rt for 30 minutes before the addition of the corresponding alcohol (1.1-5.0 eq). The reaction mixture was stirred at rt for 1-16h and then the solvent was removed in vacuo. The residue was partitioned between DCM and water and extracted with DCM. The organic layer was separated, washed consecutively with 2M sodium carbonate (or 1N NaOH), 1N HCl, brine, dried over MgSO4, and evaporated. Protocol C. To a solution of the corresponding carboxylic acid 7-9 (0.25 mmol) in THF or DCM (1 mL) cooled to 0 C was added 1-chloro-N,N,2-trimethyl-1-propenylamine, (0.5 mmol, 2.0 eq). The reaction mixture was stirred for 1-3h while warming up to rt, followed by addition of the corresponding alcohol (1.2 eq). The reaction mixture was stirred at rt for 1-16h and then the solvent was evaporated under reduced pressure. The residue was diluted with EtOAc and washed with saturated NaHCO3. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure.

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Reference£º
Article; Boland, Sandro; Defert, Olivier; Alen, Jo; Bourin, Arnaud; Castermans, Karolien; Kindt, Nele; Boumans, Nicki; Panitti, Laura; Van De Velde, Sarah; Stalmans, Ingeborg; Leysen, Dirk; Bioorganic and Medicinal Chemistry Letters; vol. 23; 23; (2013); p. 6442 – 6446;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Tetrahydro-2H-pyran-3-ol (0.051 g, 0.499 mmol was taken into THF (1 mL) followed by the addition of 1M potassium butoxide in THF (0.5 mL, 0.5 mmol). The mixture was stirred for about 10 min, then (i?)- 2-(2-fluoropyridin-4-yl)-8-phenyl-7,8-dihydro-6H-pyrrolo[2′,r:2,3]imidazo[4,5-6]pyridine (0.055 g, 0.166 mmol, Preparation 84) in THF (1 mL) was added and the mixture was heated at about 120 C for about 20 min in a microwave. The reaction was cooled to rt, quenched with water and extracted with 100 mL EtOAc. The organics were collected, passed through a phase separator, concentrated under reduced pressure and the residue purified via silica gel chromatography eluting with 75-100% EtOAc/heptanes to afford the title compound (0.03 g, 45 %); LC/MS (Table 1, Method ab) Rt = 0.89 min; MS m/z: 413 (M+ H)+. (TNF IC50 = B).

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Reference£º
Patent; ABBVIE INC.; BREINLINGER, Eric, C.; COX, Phil, B.; DAANEN, Jerome; DIETRICH, Justin; DJURIC, Stevan; DOMBROWSKI, Amanda, W.; FRANK, Kristine, E.; FRIEDMAN, Michael, M.; GOMTSYAN, Arthur; LI, Huan-Qui; LONGENECKER, Kenton; OSUMA, Augustine; ROWLEY, Ann, Marie; SCHMIDT, Robert; VASUDEVAN, Anil; WILSON, Noel; (378 pag.)WO2016/168641; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics