Category: 24621-61-2

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO106,mainly used in chemical industry, its synthesis route is as follows.,24621-61-2

EXAMPLE 38 2-((3S)-3-Hydroxy- 1-butyloxy)-3-(4-methylsulfonyl)phenyl-5-trifluoromethylpyridine To a solution of (S)-1,3-butanediol (807 mg) in DMF (10 mL) at 0 C. was added potassium t-butoxide (7.2 mL of a 1M solution in THF). After 1 h, the mixture was cooled to -20 C. and then 2-chloro-3-(4-methylsulfonyl)phenyl-5-trifluoromethylpyridine (1 g) was added as a solid. The resulting mixture was stirred for 24 h, warming to r.t. To the mixture was added saturated NH4Cl and the mixture was extracted with ethyl acetate. The organics were dried (MgSO4) and concentrated. Flash chromatography (1:1 hexane/ethyl acetate) provided the title compound as a white solid (323 mg). 1 H NMR (300 MHz, acetone-d6): d 1.15 (d, 3H), 1.75-2.00 (m, 2H), 3.15 (s, 3H), 3.65 (d, 1H), 3.85-4.00 (m, 1H), 4.60 (dd, 2H), 7.95 (d, 2H), 8.03 (d, 8.10 (d, 1H), 8.57 (d, 1H).

With the complex challenges of chemical substances, we look forward to future research findings about (S)-Butane-1,3-diol,belong chiral-oxygen-ligands compound

Reference£º
Patent; Merck Frosst Canada & Co.; US6046217; (2000); A;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO157,mainly used in chemical industry, its synthesis route is as follows.,24621-61-2

Example 7A (2S)-4-((tert-butyl(dimethyl)silyl)oxy)-2-butanol A 0 C. solution of (S)-(+)-1,3-butanediol (2.1 g, 23.3 mmol), imidazole (1.74 g, 25.6 mmol), and N,N-dimethylformamide (1.0 mL) in dichloromethane (40 mL) was treated with tert-butyl-dimethylsilyl chloride (3.68 g, 23.3 mmol). The reaction mixture was warmed to room temperature, stirred overnight, quenched with saturated aqueous ammonium chloride and extracted with dichloromethane. The combined dichloromethane layers were dried (MgSO4), filtered and concentrated to afford of the desired product of sufficient purity for subsequent use without further purification in near quantitative yield. MS (DCI/NH3) m/z 205 (M+H)+; 1H NMR (300 MHz, CDCl3) delta3.95 (m, 1H), 3.79 (m, 2H), 3.27 (br s, 1H), 1.56 (m 2H), 1.11 (d, 3H), 0.82 (s, 9H), 0.016 (s, 6H).

With the complex challenges of chemical substances, we look forward to future research findings about (S)-Butane-1,3-diol,belong chiral-oxygen-ligands compound

Reference£º
Patent; Bennani, Youssef L.; Black, Lawrence A.; Dwight, Wesley J.; Faghih, Ramin; Gentles, Robert G.; Liu, Huaqing; Phelan, Kathleen M.; Vasudevan, Anil; Zhang, Henry Q.; US2001/49367; (2001); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Name is (S)-Butane-1,3-diol, as a common heterocyclic compound, it belongs to chiral-oxygen-ligands compound, and cas is 24621-61-2, its synthesis route is as follows.,24621-61-2

To a solution of (S)-1,3-butanediol (807 mg) in DMF (10 mL) at 0C was added potassium t-butoxide (7.2 mL of a 1M solution in THF). After 1 h, the mixture was cooled to -20C and then 2-chloro-3-(4-methylsulfonyl)phenyl-5-trifluoromethylpyridine (1 g) was added as a solid. The resulting mixture was stirred for 24 h, warming to r.t. To the mixture was added saturated NH4Cl and the mixture was extracted with ethyl acetate. The organics were dried (MgSO4) and concentrated. Flash chromatography (1:1 hexane/ethyl acetate) provided the title compound as a white solid (323 mg).1H NMR (300 MHz, acetone-d6): d 1.15 (d, 3H), 1.75-2.00 (m, 2H), 3.15 (s, 3H), 3.65 (d, 1H), 3.85-4.00 (m, 1H), 4.60 (dd, 2H), 7.95 (d, 2H), 8.03 (d, 2H), 8.10 (d, 1H), 8.57 (d, 1H).

With the complex challenges of chemical substances, we look forward to future research findings about (S)-Butane-1,3-diol

Reference£º
Patent; MERCK FROSST CANADA & CO.; EP1012142; (2004); B1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

It is a common heterocyclic compound, the chiral-oxygen-ligands compound, (S)-Butane-1,3-diol, cas is 24621-61-2 its synthesis route is as follows.,24621-61-2

General procedure: (R)-Ethyl 3-hydroxybutyrate (2.1 g, 16 mmol) and (R)-1,3 butanediol(1.0 g, 11 mmol) were combined and incubated with CAL-B (0.2 g,400 U) at 80 torr without solvent in a rotary evaporator. The reaction was monitored by withdrawing 5 muL portions of the reaction mixture,which were dissolved in 1.0 mL methanol for analysis by GC-MS. Upon consumption of the diol, the reaction mixture was taken up in dichloromethane,the beads were filtered and washed, and the solventremoved by rotary evaporation. Excess (R)-ethyl 3-hydroxybutyratewas removed by heating to 60 deg C under reduced pressure (1 torr).The residue was suspended in ethyl acetate, treated with activated carbon and filtered to yield (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrateas a clear oil (1.2 g, 62%).

With the complex challenges of chemical substances, we look forward to future research findings about (S)-Butane-1,3-diol

Reference£º
Article; Budin, Noah; Higgins, Erin; DiBernardo, Anthony; Raab, Cassidy; Li, Chun; Ulrich, Scott; Bioorganic Chemistry; vol. 80; (2018); p. 560 – 564;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

(S)-Butane-1,3-diol, cas is 24621-61-2, it is a common heterocyclic compound, the chiral-oxygen-ligands compound, its synthesis route is as follows.,24621-61-2

Preparation of (3S)-1-p-Toluenesulfonyloxy-3-triethylsilyloxy-butane (2b); To a stirred, solution of the(S)-(+)-1,3-butanediol 1b (1 g, 11.1 mmol), DMAP (30 mg, 0.25 mmol) and Et3N (4.6 mL, 3.33 g, 33 mmol) in anhydrous methylene chloride (20 mL) p-toluenesulfonyl chloride (2.54 g, 13.3 mmol) was added at 0 C. The reaction mixture was stirred at 4 C. for 22 h. Methylene chloride was added and the mixture was washed with water, dried (Na2SO4) and concentrated under reduced pressure. A residue was chromatographed on silica gel with hexane/ethyl acetate (8:2, then 1:1) to afford the tosylate (2.31 g, 85% yield) as a colorless oil.

24621-61-2 is used more and more widely, we look forward to future research findings about (S)-Butane-1,3-diol

Reference£º
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; US2012/283228; (2012); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

(S)-Butane-1,3-diol, cas is 24621-61-2, it is a common heterocyclic compound, the chiral-oxygen-ligands compound, its synthesis route is as follows.,24621-61-2

Example 25 (4-{(R)-3-[(2-CHLORO-3-TRIFLUOROMETHYL-BENZYL)-2, 2-DIPHENYLETHYL-AMINO]-BUTOXY}-INDOL-1- YL) acetic acid hydrochloride salt a) Toluene-4-sulfonic acid (S)-3-hydroxy-butyl ester To a solution of (S)-1, 3-butanediol (2.0 g, 22.0 MMOL) and Et3N (4.6 mL, 33.0 MMOL) in CH2CI2 (20 mL) at-20 C was added p-toluenesulfonyl chloride (4.46 g, 23.0 MMOL) and the reaction mixture was then warmed to RT and stirred overnight. The reaction mixture was washed with H20 and brine, dried over NA2SO4, filtered, and concentrated to give the title compound as a yellow oil (5.2 G, 96%)a) Toluene-4-sulfonic acid (S)-3-hydroxy-butyl ester To a solution of (S)-1, 3-butanediol (2.0 G, 22.0 MMOL) and Et3N (4.6 mL, 33.0 MMOL) in CH2CI2 (20 mL) at-20 C was added p-toluenesulfonyl chloride (4.46 g, 23.0 MMOL) and the reaction mixture was then warmed to RT and stirred overnight. The reaction mixture was washed with H20 and brine, dried over NA2SO4, filtered, and concentrated to give the title compound as a yellow oil (5.2 G, 96%)

24621-61-2 is used more and more widely, we look forward to future research findings about (S)-Butane-1,3-diol

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/23196; (2005); A2;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

As a common heterocyclic compound, it belongs to chiral-oxygen-ligands compound, name is (S)-Butane-1,3-diol, and cas is 24621-61-2, its synthesis route is as follows.,24621-61-2

Example 1; Preparation of (3S)-1-p-Toluenesulfonyloxy-3-triethylsilyloxy-butane (2); To a stirred solution of the (S)-(+)-1,3-butanediol 1 (1 g, 11.1 mmol), DMAP (30 mg, 0.25 mmol) and Et3N (4.6 mL, 3.33 g, 33 mmol) in anhydrous methylene chloride (20 mL) p-toluenesulfonyl chloride (2.54 g, 13.3 mmol) was added at 0 C. The reaction mixture was stirred at 4 C. for 22 h. Methylene chloride was added and the mixture was washed with water, dried (Na2SO4) and concentrated under reduced pressure. A residue was chromatographed on silica gel with hexane/ethyl acetate (8:2, then 1:1) to afford the tosylate (2.31 g, 85% yield) as a colorless oil.

24621-61-2 is used more and more widely, we look forward to future research findings about (S)-Butane-1,3-diol

Reference£º
Patent; DeLuca, Hector F.; Clagett-Dame, Margaret; Plum, Lori A.; Chiellini, Grazia; Grzywacz, Pawel; US2008/81799; (2008); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO296,mainly used in chemical industry, its synthesis route is as follows.,24621-61-2

Example 4 : (R)-2-(3-{3-[[2-Chloro-3-(trifluoromethyl) benzyl] (2,2- diphenylethyl) amino]-1-methyl-propoxy}-phenyl) acetic acid methyl ester ; a) Toluene-4-sulfonic acid- (S)-3-hydroxy-butyl ester; To a stirring solution of (S)-1, 3-butanediol (1.0 g, 0.01 mmol) and triethylamine (1.39 g, 0.014 mmol) in dichloromethane (10 mL) at-20C was added dropwise p-toluenesulfonyl chloride and the mixture was stirred for 2 h. The reaction mixture was then warmed to RT and stirred overnight. The reaction mixture was poured into cold H2O (20 mL), and extracted three times with dichloromethane. The organic extracts were then washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give 2.6 g (96% yield) of title compound as an oil. MS (ESI) 244.8 (M+). The crude tosylat was used without further purification.

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-Butane-1,3-diol,belong chiral-oxygen-ligands compound

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2003/82802; (2003); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO455,mainly used in chemical industry, its synthesis route is as follows.,24621-61-2

Example 1 Preparation of (3S)-1-p-Toluenesulfonyloxy-3-triethylsilyloxy-butane (2)To a stirred solution of the (S)-(+)-1,3-butanediol 1 (1 g, 11.1 mmol), DMAP (30 mg, 0.25 mmol) and Et3N (4.6 mL, 3.33 g, 33 mmol) in anhydrous methylene chloride (20 mL) p-toluenesulfonyl chloride (2.54 g, 13.3 mmol) was added at 0 C. The reaction mixture was stirred at 4 C. for 22 h. Methylene chloride was added and the mixture was washed with water, dried (Na2SO4) and concentrated under reduced pressure. A residue was chromatographed on silica gel with hexane/ethyl acetate (8:2, then 1:1) to afford the tosylate (2.31 g, 85% yield) as a colorless oil.To a stirred solution of the tosylate (2.31 g, 9.5 mmol) and 2,6-lutidine (1.2 mL, 1.12 g, 10.5 mmol) in anhydrous methylene chloride (15 mL) triethylsilyl trifluoromethanesulfonate (2.1 mL, 2.51 g, 9.5 mmol) was added at -50 C. The reaction mixture was allowed to warm to room temperature (4 h) and stirring was continued for additional 20 h. Methylene chloride was added and the mixture was washed with water, dried (Na2SO4) and concentrated under reduced pressure. A residue was chromatographed on silica gel with hexane/ethyl acetate (97:3) to afford the product 2 (2.71 g, 80% yield) as a colorless oil:[alpha]D+18.0 (c 2.38, CHCl3); 1H NMR (400 MHz, CDCl3) delta 7.77 (2H, d, J=8.2 Hz, o-HTs), 7.33 (2H, d, J=8.2 Hz, m-HTs), 4.10 (2H, t, J=6.1 Hz, 1-H2), 3.90 (1H, m, 3-H), 2.43 (3H, s, MeTs), 1.72 (2H, m, 2-H2), 1.10 (3H, d, J=6.2 Hz, 4-H3), 0.88 (9H, t, J=8.0 Hz, 3¡ÁSiCH2CH3), 0.50 (6H, q, J=8.0 Hz, 3¡ÁSiCH2CH3); 13C NMR (100 MHz) delta 144.62 (s, p-CTs), 133.03 (s, i-CTs), 129.72 (d, m-CTs), 127.82 (d, o-CTs), 67.78 (t, C-1), 64.46 (d, C-3), 38.47 (t, C-2), 23.82 (q, C-4), 21.52 (q, MeTs), 6.71 (q, SiCH2CH3), 4.77 (t, SiCH2CH3); MS (EI) m/z 359 (5, MH+), 329 (87, M+-C2H5), 259 (100), 233 (54), 197 (50), 179 (74), 163 (40), 149 (48), 135 (38), 115 (53), 91 (71); exact mass calculated for C15H25O4SSi (M+-C2H5) 329.1243, found 329.1239.

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-Butane-1,3-diol,belong chiral-oxygen-ligands compound

Reference£º
Patent; DeLuca, Hector F.; Clagett-Dame, Margaret; Plum, Lori A.; Chiellini, Grazia; Grzywacz, Pawel; US2009/170821; (2009); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

(S)-Butane-1,3-diol, cas is 24621-61-2, it is a common heterocyclic compound, the chiral-oxygen-ligands compound, its synthesis route is as follows.,24621-61-2

S- (+)-1, 3-butanediol (96 mg, 1.065 mmol) in 3 ml of pyridine was cooled in an ice-water bath and 4,4′-dimethoxytrityl chloride (430 mg, 1.27 mmol) was added thereto. The resulting mixture was stirred for 6 hours at room temperature. 10 ml of 5% NAHCO3 was added thereto and the resulting solution was extracted with 15 ml of ethyl acetate. The organic layer was dried over MGS04 and evaporated under a reduced pressure. The resulting yellow liquid residue was purified by silica gel column chlomatography (eluent-ethyl acetate: hexane = 1: 3) to obtain the title compound (401 mg, 1.02 mmol) in a yield of 96%. Rf= 0.3 (ethyl acetate: Hexane = 1 : 2); IR (NACI) nu (cm-1) 3462, 3059, 3034, 2959, 2927, 2848,2835, 1607,1508, 1250; 1H NMR (Acetone-d6) delta 7.49 (br, 1H), 7.46 (br, 1H), 7.36-7. 18 (m, 7H), 6.86 (t, 2H, J=2. 6Hz), 6.84 (t, 2H, J=2.6Hz), 3.93 (br, 1H), 3.73 (s, 6H), 3. 50 (br, 1H), 3.28-3. 14 (m, 2H), 1.73 (m, 2H), 1. 11 (d, 3H, J=6. 2Hz) ; 13C-NMR (75.5 MHz, Acetone-d6) delta 158. 1, 145. 3, 136. 1, 136.0, 129.5, 127. 6, 127.2, 126. 1, 112.5, 85. 4, 64. 2, 60. 6, 54. 2, 39.0, 23.1; MS-FAB (m/z): [M] + calcd for C25H28O4, 392; found 392.; [alpha] 21D = +17. 6 (c 1.0, CHCl3)

With the rapid development of chemical substances, we look forward to future research findings about (S)-Butane-1,3-diol

Reference£º
Patent; POSTECH FOUNDATION; WO2004/63208; (2004); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate