Chiral oxygen ligands

New downstream synthetic route of 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.

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

(S)-Methylethylene Bis(methylsulfonate), CAS 270577-16-7, Compound A Scheme 1,was prepared from (S)-(+)-1,2-propanediol (CAS 4254-15-3, Sigma Aldrich Chemical Company) and methane sulfonyl chloride (CAS 124-63-O, Sigma Aldrich Chemical Company) according to the procedure of T. Harada, T. Mai, T. Tuyet, and A. Oku, Organic Letters (2000), 2(9), 1319-1322.

Reference£º
Patent; Kent State University; Kent Displays Incorporated; US2012/273725; (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

A new synthetic route of 538-58-9

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.

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: General procedure: A mixture of 8a (70.3 mg, 0.3 mmol) and 1a (172.2 mg, 0.36 mmol) in DMSO (2.0 mL) was stirred under nitrogen atmosphere for 5 min at room temperature. Then DBU (0.065 mL, 0.45 mmol), followed by DMSO (1 mL), was added and the resulting mixture was heated to 80 C in N2 atmosphere. After the reaction was complete, the mixture was filtered through a thin layer (30 mm) of silica gel (100-200 mesh) and washed with DCM. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography (PE/EtOAc=60/1) to afford 11a (72.1 mg, 76%).

Reference£º
Article; Shu, Zhen-Cao; Zhu, Jian-Bo; Liao, Saihu; Sun, Xiu-Li; Tang, Yong; Tetrahedron; vol. 69; 1; (2013); p. 284 – 292;,
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

The origin of a common compound about (S)-Butane-1,3-diol

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.

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).

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

Some scientific research about (2S,3S)-Butane-2,3-diol

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,(2S,3S)-Butane-2,3-diol,19132-06-0,its application will become more common.

19132-06-0 A common heterocyclic compound, 19132-06-0,(2S,3S)-Butane-2,3-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.

To a 500-mL, 3-necked-RBF (equipped with a H20-cooled refluxcondenser and an HC1 trap) was added (2s,3s)-(+)-2,3-butanediol (Aldrich; 15.00mL, 166 mmol) and CC14 (120 mL). SOC12, reagentplus (14.57 mL, 200 mmol)was then added drop wise via a syringe over a period of 20 mm and the resultingmixture was heated to 98C for 45 mm, then allowed to cool to rt. The reactionmixture was then cooled in an ice/H20 bath, MeCN (120 mL) and H20 (150 mL) were added followed by ruthenium(III) chloride (0.035 g, 0.166 mmol). Sodium periodate (53.4 g, 250 mmol) was then added slowly portion wise over 30 mm. The resulting biphasic brown mixture was stirred vigorously while allowed toreach rt for a period of 1.5 h (internal temperature never increased above rt). TLC (50% EtOAc in heptanes) showed complete conversion. The cmde mixture was then poured into ice H20 and extracted twice with 300 mL of Et20. The combined organic layers were washed once with 200 mL of sat. sodium bicarbonate, washed once with 200 mL of brine, dried over Na2504, andconcentrated by rotary evaporation to give (45,55)-4,5-dimethyl-1,3,2- dioxathiolane 2,2-dioxide (21.2 g, 139 mmol) as a red oil.

Reference£º
Patent; AMGEN INC.; HARRINGTON, Paul E.; ASHTON, Kate; BROWN, Sean P.; KALLER, Matthew R.; KOHN, Todd J.; LANMAN, Brian Alan; LI, Kexue; LI, Yunxiao; LOW, Jonathan D.; MINATTI, Ana Elena; PICKRELL, Alexander J.; STEC, Markian M.; TAYGERLY, Joshua; (991 pag.)WO2018/183418; (2018); 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

Some scientific research about (S)-Propane-1,2-diol

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.

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.

To separate the propylene glycol enantiomers on a chiral gas chromatography column, they were derivatized with acetic anhydride to the methyl esters. Into a small vial equipped with a Teflon lined stir bar was added 1 mL diethyl ether and equal amounts (5-10 drops) propylene glycol, pyridine, and acetic anhydride. The reaction mixture was stirred 3 hours at room temperature, washed with deionized 0 (3 x 1 mL) and dried over Na2S04. The derivatized product was then analyzed via gas chromatography. The diacetate was obtained with an ee of 97percent when (R,i?)-(Cl-salcy)CoN03 was used, and with an ee of 96percent when (5,S)-(Cl-salcy)CoN03 was used, indicating that both enantiomers produced highly regioregular poly(propylene succinate).

Reference£º
Patent; CORNELL UNIVERSITY; COATES, Geoffrey; WHITEHEAD, Julie; (60 pag.)WO2016/25675; (2016); 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

New downstream synthetic route of 19132-06-0

A common heterocyclic compound, 19132-06-0,(2S,3S)-Butane-2,3-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. 19132-06-0

To a 500-mL, 3-necked round-bottomed flask (equipped with a water- cooled reflux condenser and an HCI trap) was added (2s,3s)-(-f-)-2.3-butanediol (Aldrich, Milwaukee Wisconsin)(1500 nil, 166 mniol) and CCI4 (120 ml). Thionyl chloride. reagentplus (14.57 ml, 200 mmoi) was then added drop wise viaa syringe over a period of 20 minutes and the resulting mixture was heated to98 C for 45 minutes, then it was allowed to cool to room temperature. Rf ofintermediate == 0.42 eluting with 50% EtOAc in heptanes; use KMNO4 to visualizecompound, The reaction mixture was then cooled in an ice-water bath. MeCN(120 mL) and water (150 rnL) were added followed by ruthenium(111) chloride(0.035g. 0.166 nunol). Sodium periodate (53.4 g, 250 rnmol) was then addedslowly portion wise over 30 minutes. The resulting biphasic brown mixture was stirred vigorously whie allowed to reach room temperature for a period of 1.5 hour (internal temperature never increased above room temperature). TLC (50% EtOAc in heptanes) showed complete conversion. The crude mixture was thenpoured into ice water and extracted twice with 300 ml of diethyl ether. The combined organic layers were washed once with 200 ml of saturated sodium bicarbonate, washed once with 200 nil of brine, dried over sodium sulfate and concentrated by rotary evaporation to give (4S.5 S)-4,5-dimethyi- 1,3,2- dioxathiolane 2,2-dioxide (21.2 g, 139 mmoi) as a red oil.

Reference£º
Patent; AMGEN INC.; BROWN, Sean P.; BEDKE, David Karl; DEGRAFFENREID, Michael R.; FU, Jiasheng; LI, Zhihong; GONZALEZ LOPEZ DE TURISO, Felix; GONZALEZ BUENROSTRO, Ana; GRIBBLE, Jr., Michael W.; JOHNSON, Michael G.; KOHN, Todd J.; LI, Kexue; LI, Yunxiao; LIZARZABURU, Mike Elias; REW, Yosup; TAYGERLY, Joshua; WANG, Yingcai; YAN, Xuelei; YU, Ming; ZHU, Jiang; ZANCANELLA, Manuel; JIAO, Xian Yun; ZHU, Liusheng; WANG, Xianghong; MEDINA, Julio C.; DUQUETTE, Jason A.; HOUZE, Jonathan B.; VIMOLRATANA, Marc; CARDOZO, Mario G.; CHENG, Alan C.; (2426 pag.)WO2017/147410; (2017); 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

The origin of a common compound about 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).

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

Some scientific research about 4254-15-3

Example 29; N-r(2Z)-3-butviri.31thiazolor4.5-clpyridin-2(3H)-ylidenel-2-(r(2S)-2-hvdroxypropylloxyl-5 -(trifluoromethyl)benzamide; (S)-propane-l,2-diol (52 mg, 0.68 mmol) in THF (1 mL) was treated with NaH (60percent dispersion; 27 mg, 0.68 mmol) at room temperature for 20 minutes. The mixture was cooled to O0C and a solution of Example 2OB (90 mg, 0.23 mmol) in THF (1 mL) was added. The mixture was allowed to warm to room temperature, and stirred for 4 hours. The mixture was diluted with saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (2 x 30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography using an Analogix.(R). Intellifiash280 .(TM). (SiO2, 0-100 percent ethyl acetate in hexanes) to afford 19 mg (19percent) of the title compound. 1H NMR (500 MHz, CDCl3) delta ppm 1.04 (t, J=7.48 Hz, 3 H) 1.28 (d, J=6.41 Hz, 3 H) 1.47 – 1.59 (m, 2 H) 1.88 – 1.98 (m, 2 H) 3.87 (t, J=8.85 Hz, 1 H) 4.21 – 4.31 (m, 1 H) 4.35 (dd, J=9.15, 2.75 Hz, 1 H) 4.51 – 4.59 (m, 2 H) 7.12 (d, J=8.85 Hz, 1 H) 7.72 (dd, J=8.54, 2.14 Hz, 2 H) 8.51 (d, J=I.83 Hz, 2 H) 8.75 (s, 1 H); MS (DCI/NH3) m/z 454 (M+H)+.

Reference£º
Patent; ABBOTT LABORATORIES; FROST, Jennifer, M.; LATSHAW, Steven, P.; DART, Michael, J.; CARROLL, William, A.; PEREZ-MEDRANO, Arturo; KOLASA, Teodozyj; PATEL, Meena; NELSON, Derek, W.; LI, Tongmei; PEDDI, Sridhar; WANG, Xueqing; LUI, Bo; WO2010/71783; (2010); 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 new synthetic route of (2S,3S)-Butane-2,3-diol

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19132-06-0,(2S,3S)-Butane-2,3-diol,its application will become more common.