Category: Tetrahydropyrans

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

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

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

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

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

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

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

951127-25-6, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

15a (342 mg, 0.656 mmol) and Intermediate 1 (236 mg, 0.722 mmol) were dissolved in N, N-dimethylacetamide (5 mL) and stirred at room temperature for 0.5 hour, A solution of sodium tris (acetoxy) borohydride (375.3 mg, 1.771 mmoL) was added to the ice bath,Stir at room temperature for 2 hours. To the reaction solution was added concentrated aqueous ammonia (10 mL) and saturated sodium chloride solution (30 mL)And the mixture was stirred for 0.5 hour. The filtrate was extracted with dichloromethane (30 mL x 3). The filter cake was dissolved with the combined organic phase, dried over anhydrous sodium sulfate, filtered and dried by rotary separation. The residue was purified by silica gel column chromatography (Dichloromethane / methanol (v / v) = 30: 1 to 20: 1, a small amount of aqueous ammonia was added) to give a yellow solid as a yellow solid 15b (200 mg, yield 59%).

951127-25-6, The synthetic route of 951127-25-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sichuan Haisco Pharmaceutical Co.,Ltd.; FAN, JIANG; ZHANG, CHEN; PENG, FEI; WU, YE; FENG, JIANCHUAN; WANG, JIANMIN; ZHENG, SUXIN; WEI, YONGGANG; YE, FEI; (350 pag.)TW2017/8220; (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.951127-25-6,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

951127-25-6, Compound 3(200 mg, 0.611 mmol) and HSCH2CH2SH (0.11 mL, 1.53 mmol) were dissolved in DCM (10 mL) and treated with BF3 etherate (0.077 mL, 0.611 mmol) at RT. The resulting solution was stirred at RT for 1 h, and quenched with sat. aq. NaHCO3 solution. The organic phase was separated andextracted with DCM for several times. Combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 60 – 90 oC PE:EtOAc =10:1) to yield the product 8 (white solid, 212 mg, 0.525 mmol, 86%). M.p. 156.6 – 159.0 (dichloromethane); Rf 0.2 (10 : 1, petroleum ether : EtOAc); [alpha]D -7.88 (c 0.165, CHCl3) ; HPLC tR 3.6min; 1H NMR (600 MHz, CDCl3) delta 7.28 (s, 1H, ArH), 6.95 (s, 2H, ArH), 4.45 (d, J = 9.0 Hz, 1H, NHBoc),4.42 (d, J = 9.9 Hz, 1H, H-1), 4.00 (dd, J = 12.0 Hz, 1.8 Hz, 1H, H-5), 3.86 (d, J = 9.0 Hz, 1H, H-2), 3.74(d, J = 11.6 Hz, 1H, H-5?), 3.34 (ddd, J = 22.8, 12.0, 5.8 Hz, 4H, Dithiolane-CH2), 2.63 (d, J = 12.9 Hz, 1H,H-3), 2.19 – 2.01 (m, 1H, H-3?), 1.27 (s, 9H, C(CH3)3); 13C NMR (151 MHz, CDCl3) delta 159.10 (d, J C-F =243.0 Hz, ArC), 156.29 (d, J C-F = 240.6 Hz, ArC), 154.55 (C=O), 128.00 (dd, J C-C-F = 15.5, 7.9 Hz, ArC),116.40 – 116.13 (m, ArC), 116.13 – 115.81 (m, ArC), 115.34 – 115.07 (m, ArC), 79.75 (C(CH3)3), 77.84(C-5), 76.01 (C-1), 64.88 (C-4), 52.80 (C-2), 46.52 (C-3), 38.96 (Dithiolane-CH2), 38.78(Dithiolane-CH2), 28.24 (C(CH3)3); HRMS (ESI+) calcd. For C18H23F2NNaO3S2+426.0980, found426.0968.

The synthetic route of 951127-25-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Li, You; Liu, Tongchao; Li, Chungang; Xiong, Bing; Zhao, Dongmei; Cheng, Maosheng; Chen, Guohua; Shen, Jingkang; Chen, Yue-Lei; Synthetic Communications; vol. 47; 4; (2017); p. 357 – 363;,
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.951127-25-6,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

55c (1.09 g, 1.78 mmol) was dissolved in N, N-dimethylacetamide (15 mL)Intermediate 1 (0.64 g, 1.95 mmol) was added to the reaction system at room temperature for 30 minutes. The reaction system was cooled to 0 C and sodium borohydrogen triacetate (0.65 g, 3.47 mmol) was added. The reaction was continued for 30 minutes and the reaction was continued at room temperature for 2 hours. The reaction solution was cooled to 0 C, water (40 mL) was added in that order, aqueous ammonia (5 mL) was added to adjust the pH to 9, and the solid was washed with water (50 mL x 3). The solid compound was dissolved in dichloromethane and treated with dichloromethane ¡Á 3), the organic phase was combined, washed with saturated brine solution (50 mL x 1), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated and purified by column chromatography (dichloromethane / methanol (v / v) = 20 : 1) to give a yellow solid 55d (0.68 g, yield 70%)., 951127-25-6

951127-25-6 tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate 44193925, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Sichuan Haisco Pharmaceutical Co.,Ltd.; FAN, JIANG; ZHANG, CHEN; PENG, FEI; WU, YE; FENG, JIANCHUAN; WANG, JIANMIN; ZHENG, SUXIN; WEI, YONGGANG; YE, FEI; (350 pag.)TW2017/8220; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics