Chiral oxygen ligands

A common heterocyclic compound, 24621-61-2,(S)-Butane-1,3-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 24621-61-2

e) (S)-4-Triisopropylsilanvloxv-butan-2-olTriethylamine (1.173 g) is added dropwise to a solution of 2.246 g triisopropylchlorosilaneand 1 g (S)-(+)-1,3-butanediol in 15 ml of dry tetrahydrofuran. The mixture is stirred for 48hours at room temperature, then is diluted with 400 ml of tert-butyl methyl ether and washedrespectively with 30 mM N HCI, 50 ml water and 50 ml of brine. The organic phase is dried(sodium sulphate), filtered and evaporated to dryness. The residue is purified by means offlash column chromatography (SiO2 60F) to provide the title compound as a colorless oil.Rf = 0.31 (EtOAc- heptane 1:5).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,24621-61-2,(S)-Butane-1,3-diol,its application will become more common.

Reference£º
Patent; SPEEDEL EXPERIMENTA AG; WO2006/5741; (2006); 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

A common heterocyclic compound, 4254-15-3,(S)-Propane-1,2-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 4254-15-3

To a stirred solution of 68 (S)-2-propanediol (1.00g, 13.14mmol) in 14 dichloromethane/69 pyridine (10:10 V/V) at -25C under argon was added dropwise 70 p-toluenesulfonyl chloride (2.51g, 13.14mmol) dissolved in 10mL of CH2Cl2 over a period of 2h. The mixture was stirred at -25C for 4h and then at room temperature for further 2h. After the reaction was completed, 30mL of CH2Cl2 were added and the mixture was shaken successively with ice-cold water, 1M 10mL 71 aqueous HCl, 15mL 72 water, saturated NaHCO3, and water, respectively. The organic phase was dried over MgSO4 and filtered and the solvent was removed under reduced pressure. The residue was purified by chromatography over silica gel using toluene/EtOAc (5/1) to give 73 product (1.70g, 56%) as white crystals. M.p: 33-35C, [alpha]D25=-12.05 (c 1, CHCl3). 1H NMR (CDCI3, ppm): delta 7.80 (d, 2H, J=8.0Hz, of OTs), 7.36 (d, 2H, J=8.0Hz, of OTs), 3.97-4.05 (m, 2H, -CHCH3-+CH2OTs (a)), 3.83-3.88 (m, 1H, CH2OTs (b)), 2.45 (s, 3H, -CH3 of OTs), 2.39 (s, 1H, OH), 1.15 (d, J=6.4Hz, 3H, -CHCH3), assignment was based on the 1H-13C HETCOR and 1H-1H COSY spectra

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4254-15-3,(S)-Propane-1,2-diol,its application will become more common.

Reference£º
Article; Meric, Nermin; Kayan, Cezmi; Guerbuez, Nevin; Karakaplan, Mehmet; Binbay, Nil Ertekin; Aydemir, Murat; Tetrahedron Asymmetry; vol. 28; 12; (2017); p. 1739 – 1749;,
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

A common heterocyclic compound, 24621-61-2,(S)-Butane-1,3-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 24621-61-2

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 H20 (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.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,(S)-Butane-1,3-diol,24621-61-2,its application will become more common.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/43939; (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

A common heterocyclic compound, 538-58-9,1,5-Diphenylpenta-1,4-dien-3-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 538-58-9

General procedure: A mixture of malononitrile (2a) (66 mg, 1 mmol), dibenzylideneacetone (6a) (234 mg, 1 mmol), tributylphosphine (25 mL, 0.1 mmol), and anhydrous CH2Cl2 (5.0 mL) was magnetically stirred in a flask under nitrogen atmosphere at room temperature. The reaction progress was monitored by thin layer chromatography (TLC) until the starting materials were completely consumed. Then, the reaction mixture was diluted with H2O (10 mL) and extracted with Et2O (3×10 mL), the organic phase was washed with brine (10 mL), dried over anhydrous Na2SO4. After the removal of the solvent under reduced pressure, the residue was subjected to chromatography on a silica gel (200-300 mesh) column using petroleum ether/ethyl acetate (4:1) as eluent to afford 7a (286 mg, 95% yield) as a light yellow solid (mp 170-171 C).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,538-58-9,1,5-Diphenylpenta-1,4-dien-3-one,its application will become more common.

Reference£º
Article; Xu, Da-Zhen; Zhan, Ming-Zhe; Huang, You; Tetrahedron; vol. 70; 2; (2014); p. 176 – 180;,
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

A common heterocyclic compound, 4254-15-3,(S)-Propane-1,2-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 4254-15-3

To a solution of (S)-1,2-propanediol (20.0 g, 0.263 mol), triethylamine (31.9 g, 0.315 mol), 4-dimethylaminopyridine (1.28 g, 10.5 mmol) in CH2Cl2 (200 mL) was added tert-butyldimethylsiloxy chloride (47.3 g, 0.315 mol) at 22 C. The mixture was allowed to stir for 18 h. The mixture was diluted with CH2Cl2, washed with water and sat. aqueous NH4Cl. The organic solution was dried over Na2SO4, filtered and concentrated under reduced pressure. Silica gel chromatography (5% ethyl acetate/hexanes) of the concentrate gave 45.0 g of the title compound as a clear oil in 90% yield.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4254-15-3,(S)-Propane-1,2-diol,its application will become more common.

Reference£º
Patent; Bristol-Myers Squibb Company; Merck & Co. Inc.; US6967196; (2005); 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

A common heterocyclic compound, 4254-15-3,(S)-Propane-1,2-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 4254-15-3

To a yellow foamy solid 4 (131.77 g, 295.11 mmol) was added (S)-(+)-1,2-propanediol (296.0 ml) and purified water (866.0 ml).Stir and slowly cool after dissolving.Stirring crystallized, filtered and drained to give a crude product 5;The crude product 5 was directly recrystallized from methyl tert-butyl ether (900 ml) without drying.After filtering to get a fine 5;Without drying, recrystallize twice with methyl tert-butyl ether (900 ml) and filter.The filter cake is washed twice with methyl tert-butyl ether.After drying, it is dried in a drying oven at 45-50C.The second boutique 5 (116.37g, 231.22mmol),HPLC purity 99.94% [HPLC normalization method:Column Agilent SB-C18 (250¡Á4.6mm 5mum);The mobile phase is mobile phase A with acetonitrile-water-trifluoroacetic acid (30:70:0.025).The mobile phase B was acetonitrile-water-trifluoroacetic acid (90:10:0.025).Gradient elution (0?20 min: A 100%?70%, 20?40 min: A 70%?10%, 40?50 min: A 10%, 50?50.1 min:A 100%, 50.1 ? 60min: A 100%,) detection wavelength 220nm;Column temperature 30C; flow rate, 1.0 ml/min], yield 78.35%.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4254-15-3,(S)-Propane-1,2-diol,its application will become more common.

Reference£º
Patent; Shanghai Modern Pharmaceutical Co., Ltd.; Zhang Guang; Shen Gang; Zou Lingyan; Fu Min; Wu Miaomiao; (13 pag.)CN107488156; (2017); 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

A common heterocyclic compound, 24621-61-2,(S)-Butane-1,3-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 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%).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,24621-61-2,(S)-Butane-1,3-diol,its application will become more common.

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

24621-61-2 A common heterocyclic compound, 24621-61-2,(S)-Butane-1,3-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

The flask was charged with (S) -butane-1,3-diol (1.00 g, 11.10 mmol) in dichloromethane (DCM) (27 mL),Triethylamine (1.347 g, 13.32 mmol),4-Dimethylaminopyridine (0.136 g, 1.110 mmol) and 4-methylbenzene-1-sulfonyl chloride (2.327 g, 12.21 mmol) were added. The reaction was stirred at room temperature for 1 hour.Quench the reaction with saturated NH 4 Cl,Extracted with DCM. The organic portion was dried over MgSO 4, filtered and concentrated under reduced pressure to give a residue which was purified by silica gel chromatography eluting with 0-50% ethyl acetate / heptane to give the product (0. 288 g, 1.179 mmol, yield 10.62%).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,24621-61-2,(S)-Butane-1,3-diol,its application will become more common.

Reference£º
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); 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

4254-15-3 A common heterocyclic compound, 4254-15-3,(S)-Propane-1,2-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Zu einer Loesung von 1.50 g (19.7 mmol) S-1, 2-Propandiol in 15 ml Dichlormethan werden 2.75 ml (19.7 mmol) Triethylamin, 0. 10 g (0. 8 MMOL) 4-N, N-Dimethylaminopyridin und 2. 97 G (19.7 mmol) tert. -Butyldimethylsilylchlorid gegeben. Die Reaktionsmischung wird fuer 16 h bei Raumtemperatur geruehrt. Anschliessend wird mit Dichlormethan verduennt und je zweimal mit Wasser, gesaettigter Ammoniumchlorid-Loesung und gesaettigter Natriumhydrogencarbonat-Loesung gewaschen. Die organische Phase wird ueber Natriumsulfat getrocknet und im Vakuum vom Loesungsmittel befreit. Der Rueckstand wird ohne weitere Reinigung in der naechsten Stufe eingesetzt. Ausbeute : 2.55 g, 80% Reinheit (54% d. Th.) GC/MS (Methode 6) : RT = 2.62 min., M/Z = 191 (M+H)+., 4254-15-3

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,(S)-Propane-1,2-diol,4254-15-3,its application will become more common.

Reference£º
Patent; BAYER HEALTHCARE AG; WO2004/80952; (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

A common heterocyclic compound, 538-58-9,1,5-Diphenylpenta-1,4-dien-3-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 538-58-9

538-58-9, Step 1. Under a nitrogen atmosphere, add 8 L of absolute ethanol and 0.112 kg of anhydrous sodium acetate to a glass reactor heated in a water bath.When the system temperature was heated to 68 C, 0.92 kg of dibenzylideneacetone obtained in Example 1 was added.After stirring for 30 minutes, add ice to the water bath heater to quickly cool the system down to 60 C.Then, 0.2 kg of palladium dichloride prepared in Example 1 was added and reacted at 60 C for 2 hours.Funnel filtration gave bis (dibenzylideneacetone) palladium (0);

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,538-58-9,1,5-Diphenylpenta-1,4-dien-3-one,its application will become more common.

Reference£º
Patent; Xi’an Kaili New Materials Co., Ltd.; Zhang Jielan; Chen Dan; Yan Pandun; Xiao Dawei; Li Yuefeng; Wan Kerou; (6 pag.)CN110256503; (2019); 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