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[ CAS No. 124752-23-4 ]

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2D
Chemical Structure| 124752-23-4
Chemical Structure| 124752-23-4
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Product Details of [ 124752-23-4 ]

CAS No. :124752-23-4MDL No. :MFCD02093270
Formula : C13H22O5 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :258.31Pubchem ID :9881588
Synonyms :

Computed Properties of [ 124752-23-4 ]

TPSA : 61.8 H-Bond Acceptor Count : 5
XLogP3 : 1.2 H-Bond Donor Count : 0
SP3 : 0.85 Rotatable Bond Count : 5

Safety of [ 124752-23-4 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 124752-23-4 ]

  • Upstream synthesis route of [ 124752-23-4 ]
  • Downstream synthetic route of [ 124752-23-4 ]

[ 124752-23-4 ] Synthesis Path-Upstream   1~33

  • 1
  • [ 124655-09-0 ]
  • [ 124752-23-4 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 0℃; for 0.5 h;
Stage #2: With pyridine; sulfur trioxide pyridine complex; dimethyl sulfoxide In dichloromethane at -5 - 20℃; for 1.16667 h;
(4R-cis)-6-(hydroxymethyl)-2,2-dimethyl- 1 ,3 -dioxane-4-acetic acid, 1 , 1 -dimethyl ethyl ester (10.0 g ,0.0385 mol) mol) was dissolved in dimethyl sulfoxide (15.0 g , 0.192 mol) and dichloromethane (100 ml) followed by cooling at 0 to -5 0C. The reaction mass was cooled for 15 min at 0 to -5 0C followed by addition of Diisopropylethyl amine( 17.42 g ,0.1347 mol) at 0 to -5 0C and continued stirring for 15 min at 0 to -5 0C. In another flask, charged pyridine-sulfur trioxide complex (12.25 g, 0.077 mol), pyridine (6.09 g, 0.077 mol) and dimethyl sulfoxide (15.0 g, 0.192 mol) at room temperature followed by stirring for 10 min. Resulting suspension was added to the above alcohol solution in dichloromethane at 0 to -5 0C and continued stirring for 1 hr at 0 to -5 0C. After the completion of reaction, water (50.0 ml) was added and stirred for 10 min. This was followed by layer separation. Aqueous layer was extracted with dichloromethane (2 x 20 ml).Dichloromethane layer was washed with water ( 3 x 100.0 ml ) followed by drying over sodium sulfate and distilled dichloromethane under vacuum at 40 to 45.0 °C.Degased mass for 1 hr at 40 to 45.0 0C under reduced pressure to obtain tertiary butyl-2-[(4R,6S)-6-formyl-2,2-dimethyl-l,3-dioxan-4-yl] acetate, compound of formula II (9.22 g, 93.0percent).
86% With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In dichloromethane; acetonitrile at 0 - 25℃; for 5.5 h; Molecular sieve (6-Formyl-2, 2-dimethyl- [1, 3] dioxan-4-yl)-acetic acid tert-butyl ester To a solution of (6-hydroxymethyl-2. 2-dimethyl-11, 3] dioxan-4-yl)-acetic acid tert- butyl ester (30.0 g, 115 mmol) at 0 °C in DCM: MeCN (10: 1,225 mL) was added 4 A molecular sieves (55 g), 4-methylmorpholine N-oxide (20. 3 g, 172.9 mmol) and tetrapropylammonium perruthenate (0.41 g, 1. 15 mmol). The reaction was warmed from 0 °C to 25 °C over 0.5 hr and then stirred at that temperature for 5 hrs. Once complete, as determined by TLC, the reaction mixture was filtered through celite and the filtrate was concentrated to a brown oil that was purified by silica gel chromatography (20-70 percent EtOAc/Hexane) to provide (6-formyl-2, 2-dimethyl- [1, 3] dioxan-4-yl)-acetic acid tert-butyl ester (25.5 g, 86percent): H-NMR (CDCI3) 09. 54 (s, 1 H), 4.30-4. 26 (m, 2 H), 2.45-2. 39 (m, 1 H), 2.33-2. 27 (m, 1 H), 1.81-1. 77 (m, 1 H), 1.46-1. 41 (m, 16 H), 1.28-1. 20 (m, 1 H).
85.9% With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In dichloromethane at -15 - 0℃; (2) step (1) to obtain compound II of the methylene chloride solution, adding 0.15g (0.99mmol) TEMPO, 2.36g (0.0198mol) potassium bromide and 16.6g (0.198mol) sodium bicarbonate, stirring and mixing after cooling to -15 °C, dropping pre-adjusting the pH to 10 sodium hypochlorite solution (175.9g (0.238mol) sodium hypochlorite solution (content 10.9percent) in terms of mass percentage concentration is 5percent sulfuric acid adjusted to pH 10), control reaction solution temperaturethe <0 °C.drop finishes, 0 °C stirring for reaction, GC tracking of the reaction, the response finishes (compound III less than0.2percent)adding quality percentage concentration is 10percent aqueous solution of sodium thiosulfate 156.5g stirring quenching reaction, the resulting organic phase after transferring, to 300g × 2 washing, to obtain light yellow clear solution, adding 50g drying by anhydrous sodium sulfate, filter, to 20g dichloromethane wash the filter cake, the spin vaporization (40 °C, -0.09 MPa) unless the solvent to obtain strawcoloured solid 46.0g, yield 90.1percent, GC purity 98.7percent, crude I is compound;
83% With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at -15 - 5℃; for 1 h; Large scale 0.02 g of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy free radical), 0.96 g of potassium bromide, 18.6 g of sodium hydrogencarbonate and 50 ml of methylene chloride were placed in a 500 ml flask, Stirred at ~ 5 ° C.After dissolving 11.64 g (44.71 mmol) of t-butyl 2 - [(4R, 6S) -6-hydroxymethyl-2,2-dimethyl- 1,3-dioxane- 4-yl] acetate in 50 ml of methylene chloride , Added to the above reaction. After cooling the reaction product to -15 ° C. or lower, 36.6 ml (53.65 mmol, 1.2 equivalent) of a 10.9percent (w / w) sodium hypochlorite aqueous solution was added dropwise at once. After the dropwise addition, stirring was carried out at 0 ° C. for 1 hour, the reaction progress degree was checked by gas chromatography (GC), the reaction product was filtered under reduced pressure, 10percent sodium thiosulfate solution (10 w / wpercent sodium thiosulfate solution) 100 ml was added and the organic layer was separated. 100 ml of a saturated sodium chloride solution was added to the organic layer, and the organic layer was further separated. After adding 150 ml of water to the organic layer and stirring for 10 minutes, the stagnant organic layer was separated, dried over anhydrous magnesium sulfate, filtered, methylene chloride as an organic solvent was distilled under reduced pressure at 40 ° C. and 3 cmHg for 10 minutes To obtain a concentrated residue 1 as an oil phase (step A).The concentrated residue 1 was adjusted to a pressure of 3 cmHg in a vacuum vacuum dryer and dried for 30 minutes at 80 ° C. without separately adjusting the humidity to obtain the title compound as pale brown crystals (Step B) . (The XRD graph of the product is shown in Figure 1 and its value is as shown in Figure 2. The DSC value of the product is shown in Figure 3.) Yield of product 83percent (8.2kg)
54% With sodium hypochlorite; TEMPOL; sodium hydrogencarbonate; potassium bromide In water; ethyl acetate at -10 - 5℃; for 1 h; Inert atmosphere Reference Example 2: tert-Butyl 2-[(4R,6S)-6-formyl-2,2-dimeihyl-1, 3-dioxane-4-yl] acetate [Show Image] To a dispersion of tert-butyl 2-[(4R,6S)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-yl] acetate (15 g, 57.6 mmol), sodium hydrogencarbonate (13.6 g, 161.3 mmol), potassium bromide (1.37 g, 11.5 mmol) and 4-hydroxy-2, 2, 6, 6-tetramethylpiperidine-1-oxyl free radical (248 mg, 1.44 mol) in ethyl acetate (150 ml), an aqueous solution of sodium hypochlorite (44.2 g, 16.7wtpercent, 70.2 mmol) was added under nitrogen stream at -10°C carefully dropwise to keep the inner temperature within 5°C. After the dropwise addition, the mixture was stirred at 0°C for 1 hour and the aqueous layer was separated. The organic layer was further diluted with ethyl acetate (100 ml), and sequentially washed with a 5percent sodium thiosulfate aqueous solution (75 ml) and water (40 ml .x. 2). Then, the organic layer was dried with anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, and the obtained crude product was purified with silica gel column chromatography (silica gel: 200 g, developing solvent: hexane / ethyl acetate = 2 / 1 by volume) to obtain the title compound (8.0 g, yield: 54percent) as white crystals. 1H-NMR (CDCl3): δ1.35(1H, q, J=12.7Hz), 1.45 (9H, s), 1.46 (3H, s), 1.49(3H, s), 1.83(1H, dt, J=2.7Hz, 12.9Hz), 2.35(1H, dd, J=5.9Hz, 15.4Hz), 2.46(1H, dd, J=7.1Hz, 15.4Hz), 4.33(1H, m), 9.58 (1H, s)
19.2 g
Stage #1: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane at 0 - 5℃; for 0.25 h;
Stage #2: With sodium hypochlorite; sodium hydrogencarbonate In dichloromethane; water at 0 - 5℃; for 1.66667 h;
Preparation of Tert-Butyl 3,5-Dideoxy-2,4-O-(1-Methylethylidene)-L-Erythro-Hexuronate
tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate (commercially available; 20 g) was added to a pre cooled (0° C. to 5° C.) mixture of 2,2,6,6-tetramethylpiperidine-1-oxyl (0.04 g), potassium bromide (1.92 g), and sodium bicarbonate (18 g) in dichloromethane (120 mL) and stirred at 0° C. to 5° C. for 15 minutes.
Aqueous sodium
hypochlorite (10percent; 40 mL) was added slowly to the resulting mixture and stirred at 0° C. to 5° C. for 30 minutes.
Sodium bicarbonate (18 g) was added to the mixture and stirred at 0° C. to 5° C. for 10 minutes, followed by the slow addition of aqueous sodium hypochlorite (10percent; 40 ml) in 30 minutes at 0° C. to 5° C.
The reaction mixture was stirred at 0° C. to 5° C. for 30 minutes.
After completion of the reaction, the reaction mixture was filtered through hyflo bed and washed with dichloromethane (20 mL).
The filtrate was washed with aqueous sodium thiosulphate (10percent; 100 mL).
The organic layer was separated and washed with de-ionized water (100 mL) and finally washed with aqueous solution of sodium chloride (10percent; 100 mL).
The organic layer was separated and concentrated under vacuum at 40° C. to give tert-butyl 3,5-dideoxy-2,4-O-(1-methylethylidene)-L-erythro-hexuronate.
Dry weight: 19.2 g.

Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 18, p. 2545 - 2548
[2] Patent: WO2008/59519, 2008, A2, . Location in patent: Page/Page column 12; 18; 23
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1247 - 1251
[4] Patent: WO2005/56004, 2005, A1, . Location in patent: Page/Page column 52; 145-146
[5] Patent: CN105503816, 2016, A, . Location in patent: Paragraph 0066; 0067; 0068
[6] Patent: JP2015/518881, 2015, A, . Location in patent: Paragraph 0041
[7] Synthetic Communications, 2003, vol. 33, # 13, p. 2275 - 2283
[8] Patent: KR101566536, 2015, B1, . Location in patent: Paragraph 0114-0115
[9] Patent: EP2351762, 2011, A1, . Location in patent: Page/Page column 9-10
[10] Tetrahedron, 2007, vol. 63, # 34, p. 8124 - 8134
[11] Patent: US2006/4200, 2006, A1, . Location in patent: Page/Page column 2-3
[12] Patent: WO2011/86584, 2011, A2, . Location in patent: Page/Page column 35
[13] Patent: US2012/323005, 2012, A1, . Location in patent: Page/Page column 15
[14] Patent: US2013/150579, 2013, A1, . Location in patent: Paragraph 0063
[15] Patent: WO2014/203045, 2014, A1, . Location in patent: Page/Page column 45; 46
[16] Journal of the American Chemical Society, 2015, vol. 137, # 45, p. 14313 - 14318
[17] Asian Journal of Chemistry, 2017, vol. 29, # 5, p. 1018 - 1022
  • 2
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Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 3, p. 513 - 516
[2] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 1, p. 364 - 372
  • 3
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  • [ 124752-23-4 ]
Reference: [1] Patent: US4970313, 1990, A,
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Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 18, p. 2545 - 2548
  • 5
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Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 18, p. 2545 - 2548
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Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 18, p. 2545 - 2548
  • 7
  • [ 147489-00-7 ]
  • [ 124752-23-4 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 1, p. 364 - 372
[2] Tetrahedron Letters, 1993, vol. 34, # 3, p. 513 - 516
  • 8
  • [ 147489-01-8 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 1, p. 364 - 372
[2] Tetrahedron Letters, 1993, vol. 34, # 3, p. 513 - 516
  • 9
  • [ 147488-99-1 ]
  • [ 124752-23-4 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 1, p. 364 - 372
[2] Tetrahedron Letters, 1993, vol. 34, # 3, p. 513 - 516
  • 10
  • [ 147488-98-0 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 1, p. 364 - 372
[2] Tetrahedron Letters, 1993, vol. 34, # 3, p. 513 - 516
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Reference: [1] Patent: WO2014/203045, 2014, A1,
[2] Patent: WO2014/203045, 2014, A1,
[3] Patent: WO2014/203045, 2014, A1,
[4] Patent: WO2014/203045, 2014, A1,
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1247 - 1251
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1247 - 1251
  • 12
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Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 3, p. 513 - 516
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  • [ 124655-08-9 ]
  • [ 124752-23-4 ]
Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 18, p. 2545 - 2548
  • 14
  • [ 154026-94-5 ]
  • [ 124752-23-4 ]
Reference: [1] Patent: WO2014/203045, 2014, A1,
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1247 - 1251
  • 15
  • [ 154026-95-6 ]
  • [ 124752-23-4 ]
Reference: [1] Patent: WO2014/203045, 2014, A1,
[2] Asian Journal of Chemistry, 2017, vol. 29, # 5, p. 1018 - 1022
  • 16
  • [ 154026-93-4 ]
  • [ 124752-23-4 ]
Reference: [1] Patent: WO2014/203045, 2014, A1,
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1247 - 1251
  • 17
  • [ 406680-96-4 ]
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Reference: [1] Patent: WO2014/203045, 2014, A1,
[2] Patent: WO2014/203045, 2014, A1,
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YieldReaction ConditionsOperation in experiment
89% With potassium carbonate In dimethyl sulfoxide at 20 - 70℃; Inert atmosphere 1) Preparation of the crude product containing the intermediate of formula (III)Under nitrogen atmosphere, 8.76 g of the compound of formula (II) was placed in a four-neck reaction flask at room temperature,Add 70mL dimethyl sulfoxide,Stirring completely dissolved, followed by the addition of 20g compound of formula (I) and 12.2g of anhydrous potassium carbonate powder,The solution was heated to 70 reaction, TLC detection and tracking, the reaction was completed, the solution was cooled to room temperature,To the solution was added 200mL of ethyl acetate and stirred for a few minutes, filtered,The filtrate was washed with pure water (100mL wash 3 times), saturated brine (100mL wash 2 times),The organic phase was separated, dried over anhydrous magnesium sulphate, filtered, the filtrate was concentrated to dryness under reduced pressure,17 g of crude product containing the intermediate of formula (III) was obtained.2) Purification of the crude product containing the intermediate of formula (III)Mass ratio of 1: 11 mass ratio of the solid obtained in step (1) was added 187mL of ethanol and n-hexane mixedSolution, absolute ethanol and n-hexane volume ratio of 1: 1,Heated to reflux, completely dissolved, stop heating, water bath down to room temperature,Then cooled in an ice bath to 0 ~ 10 ° C, filtered, the solid was dried to give a white solid 15.4g,Yield 89percent, HPLC purity of 99.41percentThe cis-isomer content is less than 0.1percent.
80% With potassium carbonate In dimethyl sulfoxide at 20℃; for 2.16 h; The compound prepared in Preparation Example 2 (11 g, 16.2 mmol) and the compound prepared in Preparative Example 1 (5.01 g, 19.4 mmol) were dissolved in 30 ml of dimethylsulfoxide, and the mixture was stirred at room temperature for 10 minutes, Potassium carbonate (3.35 g, 24.3 mmol)And the mixture was stirred at 70 ° C for 2 hours.After completion of the reaction, the temperature was maintained, 90 ml of isopropyl alcohol was added, 60 ml of H 2 O was added, refluxed at 70 to 80 ° C. for 20 minutes, and then slowly cooled to form crystals.Stir at room temperature for 30 minutes and filter the precipitate under reduced pressure.(7.48 g, yield: 80percent, HPLC: 99.5percent, white solid)
76% With potassium carbonate In toluene at 95℃; for 6 h; Adding a compound to a three-neck bottle4-(4-fluorophenyl)-5-triphenylphosphonium bromide-6-isopropyl-2-[(N-methyl-N-methylsulfonamido)]-pyrimidine 50 g,Further added 350 ml of toluene and (4R-cis)-6-[(acetoxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester 38.06 g, carbonic acid Potassium 30 grams,The temperature is raised at 95 ° C for 4.5 hours, and the temperature is lowered to room temperature.The potassium carbonate was filtered, and the solvent was evaporated to give a crude material.The crude product was refined with ethanol to give a product of 32.3 g.The yield was 76percent and the purity was 99.2percent.
75% With potassium carbonate In dimethyl sulfoxide at 25 - 75℃; for 2 h; Into a 2 L 4-necked round bottom flask, DMSO (600 ml), potassium carbonate (104 g), TPPBr (170 g) of Example 1 and BFA (65 g) were added at a temperature in the range of from about 25° C. to about 35° C. under stirring. The reaction mixture was heated to a temperature in the range of from about 70° C. to about 75° C. for about 2 hours. After completion of the reaction as determined by TLC, the reaction mixture was cooled to a temperature in the range of from about 25° C. to about 35° C. Toluene (1000 ml) was added for dilution of the reaction mixture under stirring for about 30 minutes at a temperature in the range of from about 25° C. to about 35° C. The reaction mixture was filtered, and the insoluble cake was separated. The organic layer was added to water (1000 ml) under stirring at a temperature in the range of from about 25° C. to about 35° C. and maintained for about 30 minutes. The organic layer was separated and washed twice with water (2.x.1000 ml). The organic layer was distilled in rotavapor bath at a temperature in the range of from about 50° C. to about 70° C. under in a vacuum. After distillation, methanol (750 ml) was added to the residue at a temperature in the range of from about 55° C. to about 60° C. and maintained for about 30 minutes. The reaction mixture was brought to a temperature in the range of from about 25° C. to about 30° C. by slowly Circulating water. During this time, a product precipitated out. The precipitated mass was further cooled to a temperature of about 11° C. for about 30 minutes and then filtered. The cake was washed with prechilled methanol (100 ml at a temperature of about 10° C.). The product was dried in an oven at a temperature of about 55 at a temperature of about 10° C. until the moisture content was about 1percent. The dried product appeared as an off-white crystalline solid weighing about 108 g to about 110 g. The yield was about 75percent to about 76percent, having a m.p. of 150-154° C. The IR (KBr) spectrum shows the absorption bands at 3100 cm-1 (C-H str), 2900 (C-H str), 1720 (-COO str), 1605 (-CC-str), 1150 (SO2str). The 1HNMR (CDCl3) TMS as internal standard shows the following signals δ 7.65 [m,2H,Ar-H], 7.09 [m,2H,Ar-H], 6.52 [dd,1H,ArCHCH], 5.47 [dd,1H,ArCHCH], 3.57, 3.50 [2.x.s,6H,NCH3,SO2CH3], 3.38 [hept,1H,Ar-CHMe2], 2.45-2.30 [2.x.dd,2H,CH2CO2 t-Bu], 1.55, 7.3 [dt,dd,2H,acetonide,CH2], 1.50, 1.40 [2.x.s,6H,acetonide C(CH3)2], 1.45 [s,9H,CO2C(CH3)3], 1.27 [dd,6H,ArCH(CH3)2]. The CI mass shows m/z 578 (base peak). The elemental analysis shows calculated percent C 60.29; percent H 6.98; percent N 7.27; observed percent C 60.12; percent H 6.89; percent N 7.17.
75% With potassium carbonate In dimethyl sulfoxide at 70 - 75℃; for 2 h; 600 ml of dimethyl sulfoxide, 104 grams (0.75 mole) of potassium carbonate, 170 g (0.25 mol) [4- (4-fluorophenyl) -6-isopropyl-2- [methyl (methylsulfonyl sulfo ) amino] pyrimidin-5-yl - methyl] triphenylphosphonium bromine and 65 g (0.26mol) (4R-cis) -6- aldehyde dimethyl-1,3-dioxane ring -4- acetate mixture was stirred and heated to 70-75 degrees for two hours. 1L of toluene was added, and then cooled and filtered to remove most of the inorganic impurities and phosphorus oxide. The organic phase was washed with 1L with water and then vacuum distilled to dryness and 750 ml of methanol was added to the residue, and then heated to boiling. At 25-30 degrees crystallized product. Cooled further to 11 degrees, the product isolated to give 108 g (75percent yield).

Reference: [1] Patent: CN106854201, 2017, A, . Location in patent: Paragraph 0020; 0021; 0022; 0023; 0024; 0025; 0026-0034
[2] Patent: KR101566536, 2015, B1, . Location in patent: Paragraph 0071-0072; 0120-0121
[3] Patent: CN103936680, 2016, B, . Location in patent: Paragraph 0030; 0031; 0038; 0039; 0046; 0047; 0054; 0055
[4] Patent: US2005/124639, 2005, A1, . Location in patent: Page/Page column 7-8; 10
[5] Patent: CN105461636, 2016, A, . Location in patent: Paragraph 0051; 0052
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YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In dimethyl sulfoxide at 25 - 75℃; for 5 - 7 h; In a 250 mL 4-necked round bottom flask, DMSO (150 ml), potassium carbonate (33.54 g), TBPBr (50 g) of Example 2 and BFA (20.87 g) were added at a temperature in the range of about 25° C. to about 35° C. under stirring. The reaction mixture was heated to a temperature of about 70° C. to about 75° C. for about 5 to about 7 hours. After the completion of the reaction as determined by TLC, the reaction mixture was cooled to a temperature in the range of about 25° C. to about 35° C. Toluene (250 ml) was added for dilution of the reaction mixture and stirred for about 30 minutes. The organic layer was added to water (100 ml) under stirring and maintained for 30 minutes. The organic layer was separated and washed with water (2.x.100 ml) in the same manner as described above. The organic layer was distilled in Rota vapor bath at temperature in the range of from about 50° C. to about 60° C. under vacuum. After distillation, EPA (100 ml) was added to the residue at a temperature of about 55° C. to about 60° C. and the mixture was maintained for about 30 minutes. The reaction mixture was brought to a temperature in the range of from about 25° C. to about 30° C. by Circulating room temperature water slowly. In this period, the product precipitates and the precipitated mass was further cooled to a temperature of about 10° C. for about 30 minutes, and then filtered. The cake was washed with prechilled (at a temperature of about 10° C.) IPA (50 ml). The product was dried in an oven at a temperature of about 55° C. until the moisture content was about 1percent. The dried product appeared as an off-white crystalline solid weighing about 44 g to about 45 g. The yield was about 88percent to about 90percent, and having a m.p. of 150-154° C. The IR (KBr) spectrum shows the absorption bands at 3100 cm-1 (C-H str), 2900 (C-H str), 1720 (-COO str), 1605 (-CC-str), 1150 (SO2str). The 1HNMR (CDCl3) TMS as internal standard shows the following signals δ 7.65 [m,2H,Ar-H], 7.09 [m,2H,Ar-H], 6.52 [dd,1H,ArCHCH], 5.47 [dd,1H,ArCHCH], 3.57, 3.50 [2.x.s,6H,NCH3,SO2CH3], 3.38 [hept,1H,Ar-CHMe2], 2.45-2.30 [2.x.dd,2H,CH2CO2t-Bu], 1.55, 7.3 [dt,dd,2H,acetonide,CH2], 1.50, 1.40 [2.x.s,6H,acetonideC(CH3)2], 1.45 [s,9H,CO2C(CH3)3], 1.27 [dd,6H,ArCH(CH3)2]. The CI mass shows m/z 578 (base peak). The elemental analysis shows calculated percent C 60.29; percent H 6.98; percent N 7.26; observed percent C 60.17; percent H 6.93; percent N 7.21.
Reference: [1] Patent: US2005/124639, 2005, A1, . Location in patent: Page/Page column 8-9; 10
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YieldReaction ConditionsOperation in experiment
67.7%
Stage #1: With sodium hexamethyldisilazane In tetrahydrofuran at -76 - -74℃; for 1.16667 h;
Stage #2: at -76 - 10℃; for 2.08333 h;
A mixture of DPPO (19.17 g) and THF (227 ml) were warmed briefly to 40 C. until a clear solution had formed then inerted by the sequential application of vacuum and nitrogen (5 cycles). The mixture was immersed in an acetone/CO2 bath cooling the contents to -75 C. Sodium bis(trimethylsilyl)amide (37.4 ml of 1.0 M solution in THF) was added to the reaction mixture over 10 minutes from a pressure equalising dropping funnel maintaining the temperature below -74 C and forming a red solution of the anion. THF (10 ml) was rinsed through the dropping funnel into the mixture and the mixture stirred a further 1 hour at -76 C forming a red suspension. BFA (80 ml of 13.5percent w/w toluene solution) was added in portions to the suspension over 20 minutes from a pressure equalising dropping funnel maintaining the temperature below -73 C. Toluene (20 ml) was rinised through the dropping funnel into the mixture and the mixture stirred a further 15 minutes at -76 C. The chilling bath was lowered and the suspension allowed to warm to 10 C over 1.5 hours. Glacial acetic acid (3.21 g) in water (15 g) was added in one portion raising the temperature to 18 C and dissolving all solids and the mixture was stirred a further 5 minutes. The mixture was concentrated by distillation at atmospheric pressure (jacket 110 C) to a temperature of 94 C collecting a total of 274 ml distillates. The concentrated mixture was cooled to 40 C, water (40 ml) was added and the mixture stirred for 5 minutes then allowed to settle for 15 minutes. The lower aqueous phase was discarded. Sodium hydrogen carbonate (2.99 g) in water (40 ml) was added and the mixture stirred for 5 minutes then allowed to settle for 15 minutes. The lower aqueous phase was discarded. Water (30 ml) was added and the mixture stirred for 5 minutes then allowed to settle for 15 minutes. The lower aqueous phase was discarded. The organic phase was transferred to a distillation apparatus with toluene (20 ml) and concentrated by distillation at atmospheric pressure (jacket 125-130 C) to a temperature of 116 C collecting 85 ml distillates. Vacuum was applied (400-500 mbar) and a further 16.5 ml distillates collected to a temperature of 111 C. The vacuum was released and the concentrated mixture allowed to cool to 80 C. Warm MeOH (140 ml, 50 C) was added with rapid stirring and the batch allowed to self-cool to 20 C over 30 minutes during which time a solid was deposited. The suspension was further cooled to 2 C for 30 minutes then the solid was collected by filtration on a sinter and pulled as dry as possible. The solid was washed with cold MeOH (60 ml, 2C.) and again pulled as dry as possible then transferred to a vacuum oven and dried overnight (50 C, 200 mbar); giving BEM (14.01 g, 67.7percent). 1H NMR (CDCl3, 270 MHz) 7.65 [m, 2H, ArH], 7.09 [m, 2H, ArH], 6.52 [dd, 1H, ArCH=CH], 5.47 [dd, 1H, ArCH=CH], 3.57, 3.50 [2 x s, 6H, NCH3, SO2CH3], 3.38 [hept., 1H, ArCHMe2], 2.45, 2.30 [2x dd, 2H, CH2CO2tBu], 1.55, 1.13 [dt, dd, 2H, acetonide CH2], 1.50, 1.40 [2x s, 6H, acetonide C(CH3)2], 1.45 [s, 9H, CO2C(CH3)3], 1.27 [dd 6H, ArCH(CH3)2]
61%
Stage #1: With sodium hexamethyldisilazane In tetrahydrofuran at -74℃; for 1 h;
Stage #2: at -74 - 10℃; for 3 h;
Stage #3: With acetic acid In tetrahydrofuran; water; toluene at 10 - 40℃; for 0.166667 h;
Sodium bis (trimethylsilyl) amide (1 M in tetrahydrofuran, 23 mi) is added dropwise, AT-74°C, to a suspension of the compound of formula (38) (12 g, 22.3 MMOL) in tetrahydrofuran (130 M .). STIRRING is carried out at-74°C for 1 hour and then a solution of the compound of formula (40) (6.9 g, 26.8 MMOI) in toluene (28 ML) is added dropwise. Stirring is then carried out AT-74°C for 1 hour, then warming to 10°C over the course of 1 hour and stirring for a further 1 hour at that temperature. A mixture of acetic acid (2 ml) and water (8.4 ML) is added, at 10°C, to the resulting yellow suspension and stirring is carried out at room temperature for 5 minutes. The tetrahydrofuran is then distilled off, and, at 40°C, 45 ml of water are added to the reaction mixture and vigorous stirring is carried out for 5 minutes. The aqueous phase is separated off and a solution of sodium hydrogen carbonate (2.27 G) in water (45 ml) is added to the organic phase. Vigorous stirring is again carried out for 5 minutes and then the aqueous phase is removed again. The organic phase is diluted with 250 ML of toluene, washed successively with water and saturated sodium chloride solution and dried (using NA2SO4). The salt mixture is filtered off and the filtrate is concentrated by evaporation. The concentrated residue is then purified by column chromatography on silica gel (hexane: ethyl acetate 8: 1). 2.59 G (61 percent) of the desired product (39) can be obtained in the form of colourless crystals. 'H NMR (300 MHz, CDCI3) : 0.91-1. 08 (m, 1H) ; 1.20 (d, J = 6. 7 HZ, 6H); 1. 24 (S, 3H); 1. 38 (S, 9H); 1.41 (S, 3H); 1.41-1. 56 (m, 1 H) ; 2.21 (dd, J = 15. 2, 7. 9, 1 H) ; 2. 35 (dd, J = 15. 0, 5. 0 HZ, 1H) ; 3. 27-3. 37 (m, 1H) ; 3. 43 (S, 3H); 3.52 (S, 3H); 4.17-4. 24 (m, 1H) ; 4. 47-4. 53 (m, 1H) ; 5.43 (dd, J = 16.4, 5.5 Hz, 1H) ; 6.55 (dd, J = 16.1, 0.8 Hz, 1H) ; 7.24 (dd, J = 8.8, 8.8 HZ, 2H); 7.65 (dd, J = 8.8, 5.6 Hz, 2H). 13C NMR (75 MHz, CDCI3) : 18.7, 20.6, 20.7, 27.0, 29.0, 30.9, 32.0, 35.0, 41.3, 41.4, 64.8, 68.1, 79.6, 97.7, 113.7 (JCF = 21.7 Hz), 120.0, 122.0, 131. 0 (JCF = 8.4 Hz), 133.2 (JCF = 3.2 Hz), 136.3, 156.0, 162.0 (JCF = 249 Hz), 162.2, 168.8, 173.6.
Reference: [1] Patent: US2004/49036, 2004, A1, . Location in patent: Page 3
[2] Patent: WO2004/103977, 2004, A2, . Location in patent: Page 25-26
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YieldReaction ConditionsOperation in experiment
87.3% With lithium carbonate; sodium hydride In tetrahydrofuran at 0 - 35℃; for 4.83333 h; Inert atmosphere 50 g of compound 1, 300 ml of anhydrous THF, and 0.16 g of lithium carbonate were placed in a reaction flask, protected with nitrogen, and stirred.The temperature was lowered to 0-5 ° C, and 4.6 g of NaH (60percent) was added.30 g of compound 3 ((4R-CIS)-6-formaldehyde-2,2 dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester) was dissolved in 80 ml of anhydrous T HF,It was added dropwise to the above reaction solution, and the addition was completed in 50 minutes.The reaction was kept at 0-5 ° C for 1-2 hours, and the temperature was raised to 30-35 ° C for 4 hours.TLC detection, after the reaction is completed, the temperature is lowered to 0-5 ° C,Acetic acid was slowly added dropwise to pH = 7-7.5, and 100 ml of water was added.Static, liquid separation, collecting the upper organic phase. The organic phase is washed 1-2 times with water, dried over anhydrous sodium sulfate, and filtered to remove the desiccant.The THF was distilled off under reduced pressure to give 56.6 g of a yellow oil.The crude product yield was 92.6percent. Add 125 ml of isopropanol to the above crude product, start stirring, warm up to 70 ° C until the solution is cleared, and then start to cool down after 30 minutes of heat preservation, and cool down to 5 ° C through 3 hours.Incubate for 1 hour, suction filtration, filter cake with a small amount of ice isopropanol, yield cake, dry,Obtained 53.2 g of Compound A as a white solid.HP LC = 99.2percent (E configuration) with a total yield of 87.3percent.
Reference: [1] Patent: CN108822090, 2018, A, . Location in patent: Paragraph 0052-0055; 0062-0065; 0072-0075; 0082-0085
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YieldReaction ConditionsOperation in experiment
82%
Stage #1: With sodium hexamethyldisilazane In tetrahydrofuran at -70 - -65℃; for 2 h;
Stage #2: at -70 - -65℃; for 2 h;
(1)
Preparation of tert-butyl 6-[(1E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methane sulfonyl)amino]-5-pyrimidinyl]vinyl]-2,2-dimethyl-1,3-dioxane-4-acetate (compound III)
To a 5 L four-necked flask, 2 L (8 mL/g) of tetrahydrofuran and 250 g (1 mol) of N-(5-((4,4'-tolylphosphono)-methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methyl methane sulfonamide (compound I) were sequentially added, and stirred to clearness.
The mixture was cooled down to -70˜-65° C., followed by adding 486.2 mL (1.1 mol, calculated from virtually titrated content) of sodium hexamethyldisilazide.
The system was kept at -70˜-65° C. for 2 hours, followed by adding dropwise a solution of 132.4 g (1.1 mol) of tert-butyl (4R-cis)-6-formyl-2,2-dimethyl-1,3-dioxane-4-acetate in 500 mL of tetrahydrofuran (2 mL/g).
After the addition was completed, the system was stirred at the same temperature for 2 hours, followed by warming up to about 10° C. and reacting until compound I was completely consumed.
The reaction system was then quenched with 1 L (4 mL/g) of purified water.
The liquid was separated.
The aqueous phase was extracted twice with 1.25 L (5 mL/g) of n-heptane.
The organic phase was combined, washed with 750 mL (3 mL/g) of saturated brine, and concentrated to dryness.
To the concentrated system was added 500 mL (2 mL/g) of methanol, leading to crystallization to give compound III with a purity of about 98percent, a stereo-selectivity of E/Z=99.8:0.2, and a yield of 82percent.
1H NMR (400 MHz, CDCl3) δ: 0.88 (t, J=7.4 Hz, 3H); 1.09˜1.25 (m, 7H); 1.39˜1.52 (m, 13H); 1.77 (q, J=7.3 Hz, 2H); 2.30 (dd, J1=15.1 Hz, J2=5.9 Hz, 1H); 2.45 (dd, J1=15.3 Hz, J2=7.0 Hz, 1H); 3.35˜3.39 (m, 1H); 3.51 (s, 3H); 3.56 (s, 3H); 4.28 (br, 1H); 4.41˜4.43 (br, 1H); 5.46 (dd, J1=16.2 Hz, J2=5.0 Hz, 1H); 6.51 (d, J=16.3 Hz, 1H); 7.05˜7.09 (m, 2H); 7.63˜7.66 (m, 2H); HRMS (ESI) calculated: C30H42FN3O6S; [M+1H]+=592.28, determined: 592.3.
Reference: [1] Patent: US2017/22169, 2017, A1, . Location in patent: Paragraph 0046-0047
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YieldReaction ConditionsOperation in experiment
82.3% With potassium carbonate In dimethyl sulfoxide at 70 - 80℃; A solution of 4- (4-fluorophenyl) -5- (methyl diphenylpropionylphosphonium) -6-isopropyl-2 - [(N-Methyl-N-methanesulfonamido)] - pyrimidine (Compound I), 180.0 g of (4R-cis) -6-aldehyde-2,2-dimethyl- (Compound II) 74.5 g, 125 g of potassium carbonate and 1000 g of DMSO, and the mixture was heated to 70 to 80C by stirring. The reaction was carried out until the compound (I) was completely consumed. After the reaction was completed, the filtrate was filtered and the filtrate was added with 1000 g of water, Times. Control the water bath temperature T ≤ 60 , concentrated toluene to dry to dry, crude add 900g of methanol, temperature dissolve, slow cooling crystallization, filtration, frozen methanol leaching. Control the temperature T = 40 ~ 50 dry. The dry product compound (III) was 124.3 g. Quality yield69.1percent, molar yield 82.3percent. Purity (HPLC) 99.6percent, stereoselectivity E / Z = 99.8: 0.2.
Reference: [1] Patent: CN106674281, 2017, A, . Location in patent: Paragraph 0049; 0050
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YieldReaction ConditionsOperation in experiment
77.8% With cesium fluoride In N,N-dimethyl-formamide at 20 - 120℃; for 3 h; In a 250 ml three-necked flask, a thermometer, a pH meter and a constant pressure dropping funnel and a magnetic stirrer were attached.In a reaction flask, 10 g of compound II, 100 ml of DMF and 6.5 g of tert-butyl (4R-cis) -6-aldehyde-2,2-dimethyl-1,3-dioxan-4-acetate g of cesium fluoride 0.4 g and stirred for 1 hour. Then heated to 120 , incubated for 2 hours, cooled down, poured into ice water 200ml, extracted with toluene 150ml * 2, concentrated under reduced pressure, dissolved in 100ml of methanol, cooled to room temperature, incubated for 6 hours crystallization, filtration The product (4R, 6S, E) -2- {6- [2- [4- (4- fluorophenyl) -6- isopropyl- 2- (N- methylsulfonyl) amino) 5-yl] vinyl] -2,2-dimethyl-1,3-dioxan-4-yl} acetate 11.0 g Yield 77.8percent.
Reference: [1] Patent: CN104829600, 2017, B, . Location in patent: Paragraph 0045; 0046; 0051; 0052
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YieldReaction ConditionsOperation in experiment
71.1% With potassium carbonate In dimethyl sulfoxide at 70 - 80℃; A solution of 4- (4-fluorophenyl) -5- (diphenylpropanoylphosphonium bromide) -6-isopropyl-2 - [(N-methyl-N-methanesulfonamido)] - pyrimidine(Compound I) 180.0 g,(4R-cis) -6-aldehyde-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester (Compound II), 125 g of potassium carbonate and 1000 g of DMSO were stirred and stirred to 70 ~ 80 , insulation reaction Until the compound (I) consumption is complete, after the end of the reaction, cooling filter, the filtrate by adding water 1000g, toluene extraction twice. Control water Bath temperature T ≤ 60 ° C, concentrated toluene to dry to dry crude product, the crude product by adding 900g of methanol, dissolved in temperature, slow cooling crystallization, Filter, frozen methanol leaching. Control the temperature T = 40 ~ 50 dry. The dry product compound (III) was 128.0 g. The yield was 71.1percent The molar yield was 83.0percent. Purity (HPLC) 99.7percent, stereoselectivity E / Z = 99.7: 0.3.
Reference: [1] Patent: CN106674281, 2017, A, . Location in patent: Paragraph 0042; 0043
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YieldReaction ConditionsOperation in experiment
95%
Stage #1: With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333 h; Inert atmosphere
Stage #2: at -35 - 0℃; for 21 h;
Example 3: tert-Butyl (E)-(6-[2-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine-5-yl] vinyl] (4R, 65) -2,2-dimethyl [1,3] dioxane-4-yl) acetate [Show Image] To a solution of dimethyl [4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine-5-ylmethyl] phosphonate (1.0 g, 2.25 mmol) produced in Example 1 dissolved in anhydrous tetrahydrofuran (20 ml), a 1.9 M tetrahydrofuran solution of sodium hexamethyldisilazide (1.4 ml, 2.58 mmol) was added dropwise at -78°C under nitrogen stream for 5 minutes. After the mixture was aged at -78°C for 15 minutes, a solution of tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxane-4-yl]acetate (0.7 g, 2.69 mmol) dissolved in anhydrous tetrahydrofuran (7 ml) was added thereto dropwise for 10 minutes. The device for dropwise addition was washed with anhydrous tetrahydrofuran (2 ml), and the wash fluid was added to the reaction mixture dropwise. The temperature of the reaction mixture was raised to -35°C for 3 hours, and the reaction was carried out at the same temperature for 15 hours. The temperature was raised to 0°C for 2 hour, and the mixture was aged for 1 hour. The reaction was terminated by adding a saturated ammonium chloride aqueous solution (20 ml) to the reaction mixture, and then the mixture was extracted with toluene (50 ml). The organic layer was washed distilled water (10 ml) two times and saturated brine (10 ml) two times. The quantity of the content amount of tert-butyl (E)-(6-[2-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino] pyrimidine-5-yl]vinyl](4R,6S)-2,2-dimethyl[1,3]dioxane-4-yl)acetate in the organic layer was determined with high-performance liquid chromatography; as a result, the title compound (1.2 g, yield: 95percent) was contained.
Reference: [1] Patent: EP2351762, 2011, A1, . Location in patent: Page/Page column 11
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Reference: [1] Patent: US2012/136151, 2012, A1, . Location in patent: Page/Page column 13-14
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YieldReaction ConditionsOperation in experiment
60 g With sodium methylate In tetrahydrofuran at -15 - 10℃; Alternate Method for Tert-Butyl [(4R,6S)-6-{(E)-2-[4-(4-Fluorophenyl)-2-[Methyl(Methylsulfonyl)Amino]-6-(Propan-2-Y1)Pyrimidin-5-Yl]Ethenyl}-2,2-Dimethyl-1,3-Dioxan-4-Yl]Acetate
Sodium methoxide (12.8 g) was added in lots to a pre cooled mixture of N-[4-(4-fluorophenyl)-5-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfonyl]methyl}-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide (100 g) and tert-butyl 3,5-dideoxy-2,4-O-(1-methylethylidene)-L-erythro-hexuronate (60 g) in tertrahydrofuran (500 mL) at -15° C. to 10° C.
After the completion of the reaction, the mixture was quenched with saturated aqueous solution of ammonium chloride.
To the resultant mixture, dichloromethane (500 mL) was added and the pH of the mixture was adjusted to 5.0 to 7.0 using dilute hydrochloric acid (2N).
The organic layer was washed with aqueous solution of sodium bicarbonate (5percent; 200 mL).
The organic layer was separated and concentrated under vacuum at 40° C. to 45° C. to give residue.
Methanol (1000 mL) was added to the resulting residue and stirred at 20° C. to 25° C. for 2 hours.
The product was filtered, washed with methanol (100 mL) and dried at 40° C. to 45° C. for 4 hours to 5 hours.
Dry weight: 60 g
Reference: [1] Patent: US2013/150579, 2013, A1, . Location in patent: Paragraph 0067
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Reference: [1] Patent: WO2016/125086, 2016, A1, . Location in patent: Page/Page column 29
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Reference: [1] Patent: CN105017158, 2017, B, . Location in patent: Paragraph 0030; 0034; 0035; 0042; 0043
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Reference: [1] Patent: WO2007/125547, 2007, A2, . Location in patent: Page/Page column 55; 69
[2] Patent: WO2007/125547, 2007, A2, . Location in patent: Page/Page column 58; 73-74
[3] Patent: WO2011/83495, 2011, A2, . Location in patent: Page/Page column 27
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Reference: [1] Patent: WO2007/125547, 2007, A2, . Location in patent: Page/Page column 50; 65
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Reference: [1] Patent: WO2007/125547, 2007, A2, . Location in patent: Page/Page column 52; 68-69
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