Day: November 10, 2020

185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 4; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; A three-neck-flask (0.25 L) is charged with quinidine (11 mmol), 3-isobutyl glutaric anhydride (10 mmol) and toluene (50 ml). The mixture is cooled at -55 C. Methanol (30 mmol) is added dropwise over a period of 10 min to the cooled suspension. The reaction is stirred at for 96 h. The solution is concentrated to dryness, and the resulting residue is dissolved in diethyl ether (65 ml). The solution is washed with HCl-2N, and the aqueous layer is back-extracted with ether. The combined organic layers are dried with MgSO4, and filtered. The filtrate is evaporated to dryness. Example 5; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a flame-dried 250 ml single, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30.5 vol) at -75 C. The reaction was stirred for 21 hours. The solution was concentrated to dryness, and the resulting residue was dissolved in diethyl ether (125 ml). The solution was washed with HCl-2N (40 ml¡Á3), and the aqueous layer was back-extracted with ether. The combined organic layers were evaporated until dryness, to give 3.56 g of a yellow oil of S-hemiester ((S)-3-((methoxycarbonyl)methyl)-5-methylhexanoic acid) (Optical purity 90%, Yield -91%). Example 6; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a 250 ml three-necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30.5 vol) at -50 C. The reaction was stirred for 2 hours. The slurry was washed with H2SO4-2N (40 ml¡Á3). The organic layer was evaporated until dryness, to have 3.7 g yellow oil of S-Hemiester (Optical purity 90% Yield -95%). Example 7; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a 250 ml three-necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (12.5 g, 38.6 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30.5 vol) at -78 C. The reaction was stirred for 22.5 hours. The slurry was washed with HCl-2N (40 ml¡Á3). The organic layer was evaporated until dryness, to have 3.63 g yellow oil of S-Hemiester (Optical purity 90%, Yield -93%). Example 8; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a 250 ml three necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (33 ml, 10 vol) at -78 C. The reaction was stirred for 19 hours. The solution was washed with HCl-2N (25 ml¡Á3). The organic layer was evaporated until dryness, to give 3.38 g yellow oil of S-Hemiester (Optical purity 90%, Yield -87%). Example 9; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a 250 ml three-necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30 vol) at -78 C. The reaction was stirred for 2 hours. The slurry was washed with H2SO4-2N (40 ml¡Á3). The organic layer was evaporated until dryness, to give 3.4 g yellow oil of S-Hemiester (Optical purity 95%, Yield -93%). Example 10; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; To a stirred suspension of 3-isobutyl glutaric anhydride (88 mmol) and Quinidine (100 mmol) in Toluene (30 vol) at -50 C., Methanol (273 mmol) was added drop-wise. The reaction was stirred at -50 C. for 17 h. The solution was washed with H2SO4-2N. The organic layer was evaporated to dryness to obtain S-Hemiester. (Optical purity -94%, Yield -94%). Example 11; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; To a stirred suspension of 3-isobutyl glutaric anhydride (19.3 mmol) and Quinidine (22 mmol) in Toluene (20 vol) at -50 C., Methanol (59.8 mmol) was added drop-wise. The reaction was stirred at -50 C. for 17 hours. The solution was washed with H2SO4-2N. The organic layer was evaporated to dryness to obtain S-Hemiester. (Optical purity -95%, Yield -89%). Example 12; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; To a stirred suspension of 3-isobutyl glutaric anhydride (19.3 mmol) and Quinidine (22 mmol) in Toluene (10 vol) at -50 C., Methanol (59.8 mmol) was added drop-wise. The reaction was stirred at -50 C. for 4 hours. The solution was washed with H2SO4-2N. The organic layer was evaporated to dryness to obtain S-Hemiester. (Optical purity -94%, Yield -92%). Example 13; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; To a stirred suspension of 3-isobutyl glutaric anhydride (19.3 m…

185815-59-2, The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hedvati, Lilach; Gilboa, Eyal; Avhar-Maydan, Sharon; US2007/293694; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,33821-94-2

Tetraethyl 4-(2-Tetrahydro-2H-pyranyloxy)butylene-1,1-bisphosphonate (31): 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 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; TARGANTA THERAPEUTICS, INC.; US2011/263534; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

83-87-4,83-87-4, (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

1,2,3,4,6-penta-O-acetyl-D-glucopyranose (1.678g, 4.30mmol) dissolved in DCM (10.75mL) was added hydrogen bromide (33% in acetic acid, 2.97mL) dropwise at 0C. The reaction mixture was then allowed to warm to room temperature and stir for an additional 4h. The reaction was quenched with water and the aqueous layer was extracted with DCM. The organic layers were combined and washed with water, saturated aqueous NaHCO3, brine, and then dried with sodium sulfate and concentrated under reduced pressure to afford a clear viscous oil that was immediately added to a biphasic mixture of diphyllin (1.090g, 2.87mmol) and TBAB (0.933g, 2.89mmol) in CHCl3 (100mL) and aqueous NaOH (0.1M, 100mL) at 40C. The mixture was maintained at 40C overnight. After cooling to room temperature, the layers were separated and the aqueous layer was extracted three times with CHCl3. The combined organic layers were washed with brine, dried with sodium sulfate, and concentrated under reduced pressure. Flash chromatography (silica gel, 0.3%?1% MeOH in CHCl3) afforded compound 8a (1.928g, 95%) as a white solid:

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; Woodard, John L.; Huntsman, Andrew C.; Patel, Pratiq A.; Chai, Hee-Byung; Kanagasabai, Ragu; Karmahapatra, Soumendrakrishna; Young, Alexandria N.; Ren, Yulin; Cole, Malcolm S.; Herrera, Denisse; Yalowich, Jack C.; Kinghorn, A. Douglas; Burdette, Joanna E.; Fuchs, James R.; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2354 – 2364;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

110238-91-0, Methyl tetrahydro-2H-pyran-4-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,110238-91-0

Intermediate 108: Tetrahvdro-2H-pyran-4-ylmethanolMethyl tetrahydro-2H-pyran carboxylate (SC/143233, Aldrich) (5.0 g) in dry THF (10 ml.) was added drop wise to a cooled solution of 1 M lithium aluminium hydride in THF (32 ml_), keeping the temperature below 10 0C. On completion of the addition, the exotherm was allowed to subside before allowing the reaction mixture to warm to room temperature. The reaction was then stirred for 2 hours. The reaction was quenched with water (2 ml.) added very carefully and with cooling, followed by 2N sodium hydroxide (2 ml_). To resultant suspension was then added water (100 ml.) and then extracted with dichloromethane (100 ml_, 3 times). The organic layer was separated, combined and dried by passing through a hydrophobic frit. The organic was evaporated under reduced pressure to give colourless mobile oil that was then placed under high vacuo for 30 minutes at room temperature. This gave the title compound as colourless mobile oil (2.4367 g).1 H NMR (CDCI3): 4.04-3.96 (2H, m), 3.54-3.47 (2H, m), 3.46-3.36 (2H, m), 1.82 – 1.61 (3H, m), 1.57-1.50 (1 H, m), 1.40-1.27 (2H, m)

As the paragraph descriping shows that 110238-91-0 is playing an increasingly important role.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/101867; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-94-5, 4-(Iodomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Example 16 ethyl 2-(4-bromo-5-methoxy-1H-indazol-1-yl)-3-(tetrahydro-2H-pyran-4H-yl)propanoate [Show Image] To a solution of diisopropylamine (1.35 g) in a mixed solvent of tetrahydrofuran (30 mL) and 1,3-dimethyl-3,4,5,6-tetrahydropyrimidin-2(1H)-one (15 mL) was slowly added 1.6M hexane solution (16.1 mL) of n-butyllithium at -70C under a nitrogen atmosphere. The reaction mixture was stirred at -70C for 15 min, and a solution of ethyl (4-bromo-5-methoxy-1H-indazol-1-yl)acetate (3.65 g) in tetrahydrofuran (5 mL) was slowly added thereto. The reaction mixture was stirred at – 70C for 20 min, 4-(iodomethyl)tetrahydro-2H-pyran (2.80 g) was added thereto, and the mixture was stirred overnight at room temperature. To the reaction mixture was added 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (1.36 g, yield 28%) as pale-yellow crystals from the fraction eluted with ethyl acetate-hexane (2:3, volume ratio). melting point 76-77C. MS:413(MH+)., 101691-94-5

The synthetic route of 101691-94-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP2266983; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

General procedure: To a solution of peracetylated or perbenzoylated sugars (300 mg) in 4 mL ofdry DCM at room temperature, TMSN3 (3 equiv) was added followed by the addition of AuBr3 (amounts of the catalyst are given in Table 1 and Table 2). The reaction mixture was stirred either at room temperature or heated to 55-60 C as mentioned in the Table 1 and Table 2. Then, the reaction was quenched byadding triethylamine (20 muL). The mixture was concentrated in vacuo and the crude product was purified by column chromatography.Alternatively, the reaction can be quenched by adding sodium bicarbonate solution followed by extraction with DCM(2 ¡Á 20 mL). The combined organic layers were washed with water, brine and dried over Na2SO4 and concentrated to dryness. The residue was purified by column chromatography on silica gel using petroleum ether (bp 60-70 C) and EtOAc., 83-87-4

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; Rajput, Jayashree; Hotha, Srinivas; Vangala, Madhuri; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 682 – 687;,
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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A mixture of (6a/?,9a5)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-cyclopent[4,5]imidazo[l,2-alpha]pyrazolo[4,3-e]pyrimidin-4(2H)-one (50 mg, 0.155 mmol), 4-(iodomethyl)-tetrahydro-2H-pyran (70 mg, 0.310 mmol), and Cs2CO3 (101 mg, 0.310 mmol) in DMF (1 mL) is heated in microwave at 140 0C for 30 min. After cooling, the mixture is filtered through a 0.45 mum microflter, and the filtrate is purified by a semi-preparative HPLC to give pure product as white powder. MS (ESI) m/z 421.2 [M+H]+., 101691-94-5

The synthetic route of 101691-94-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; INTRA-CELLULAR THERAPIES, INC.; WO2009/75784; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate(20 g, 116 mmol) in anhydrous THF (300 mE) was addedlithium aluminum hydride (8.8 g, 232 mmol) portionwise at0 C. The mixture was stirred at 11-13 C. for 18 h. TEC(petroleum ether: ethyl acetate=3: 1) showed no startingmaterial remaining. The mixture was quenched with water(9 mE), 10% aq. NaOH solution (9 mE) and water (18 mE)successively at 0 C., filtered and concentrated underreduced pressure to give crude 2-(tetrahydro-2H-pyran-4-yl)ethanol (11.7 g, 77%) as an oil, which was used for thenext step directly without further purification. ?H NMR(CDC13, 400 MHz): oe 3.86-3.90 (m, 2H), 3.58-3.61 (t, J=6.4Hz, 2H), 3.32-3.35 (t, J=11.6 Hz, 2H), 2.69-2.70 (m, 1H),1.61-1.63 (m, 3H), 1.54-1.60 (m, 2H), 1.43-1.45 (m, 2H).

103260-44-2, As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

Reference£º
Patent; Vitae Pharmaceuticals, Inc.; Claremon, David A.; Yuan, Jing; Zhao, Wei; Zheng, Yajun; (54 pag.)US9481674; (2016); B1;,
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.108-55-4,Dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Paclitaxel-2-O-hemiglutarate was prepared according to the method described bySundaram et al. [38]. In brief, paclitaxel (100 mg, 0.117 mM) and glutaric anhydride (13.70 mg,0.12 mM) were dissolved in 15 mL of DCM, and 10 L of dry pyridine was added to the reactionmixture as a base catalyst. The reaction was stirred under nitrogen for 48 h at room temperature.The progress of the reaction was monitored by TLC using hexane:ethyl acetate (7:3, v/v). The crudemixture was purified by silica gel chromatography. The compound was obtained as a white solid(76 mg, 95% yield). HR-MS (ESI) (m/z) [C52H57NO17]: calcd 967.3626; found 968.3479 [M + H]+

108-55-4, 108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; El-Sayed, Naglaa Salem; Shirazi, Amir Nasrolahi; Sajid, Muhammad Imran; Park, Shang Eun; Parang, Keykavous; Tiwari, Rakesh Kumar; Molecules; vol. 24; 7; (2019);,
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.

To a suspension of 3-((1R,5S,9r)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)benzamide hydrochloride (300 mg, 0.97 mmol), dihydro-2H-pyran-3(4)-one (194 mg, 1.93 mmol) in tetrahydrofuran (16 ml) was added triethylamine (0.34 ml, 2.50 mmol) and the reaction mixture was stirred at room temperature for 20 minutes. Sodium triacetoxyborohydride (614 mg, 2.89 mmol) was added and the mixture stirred at room temperature overnight. The reaction was quenched with aqueous solution of sodium hydrogen carbonate and extracted with dichloromethane (*3). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica chromatography eluting with 1-5% methanol in dichloromethane. The enantiomers were separated by chiral supercritical fluid chromatography to give 3-((1R,5S,9s)-9-methoxy-3-((S)-tetrahydro-2H-pyran-3-yl)-3-azabicyclo[3.3.1]nonan-9-yl)benzamide (81 mg, 25% yield) and 3-((1R,5S,9R)-9-methoxy-3-((R)-tetrahydro-2H-pyran-3-yl)-3-azabicyclo[3.3.1]nonan-9-yl)benzamide (71 mg, 19% yield). The stereochemistry was arbitrarily assigned.

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; Alkermes, Inc.; Wynn, Thomas Andrew; Alvarez, Juan C.; Moustakas, Demetri Theodore; Haeberlein, Markus; Pennington, Lewis D.; US2019/241524; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics