Category: 68327-04-8

Synthetic Route of 68327-04-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 68327-04-8, name is (1S,2S)-2-Aminocyclopentanol hydrochloride, molecular formula is C5H12ClNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Examples of Synthesis of Carboxamides from Diketoacid Precursor; Representative Example 1; (l S,2S)-4-(5-(2,4-difluorobenzyl)-l -(2-fluorobenzyl)-2-oxo-l,2-dihydropyridin-3-yl)-2- hydroxy-N-(2-hydroxycyclopentyl)-4-oxobut-2-enamide (9).; To a chilled solution of the 4-(l-(2-fluorobenzyl)-5-(4-fluorobenzyl)-2-oxo-l ,2- dihydropyridin-3-yl)-2-hydroxy-4-oxobut-2-enoic acid 8 (150 mg, 0.338 mmol) indimethyl formamide (DMF) (2.0 mL), was added hydroxybenzotriazole (HOBT) (50 mg, 0.372 mmol), followed by l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride EDCI-HCl (71 mg, 0.372 mmol). The resulting mixture was stirred for 30 min. A solution of ( l S,2S)-(+)-trans-2-aminocyclopentanol hydrochloride and NaHC03 (31 mg, 0.372 mmol) was added. The resulting mixture was stirred for 2h at 0- 5 C. Thin layer chromatography 05918344(TLC) analysis indicated completion, hence cold water was added to the reaction mixture and then extracted with ethyl acetate (2 x 20 m L). The combined organic phase was separated and washed with water twice, then once with IN HC1 solution, then saturated aqueous NaHCO.? solution. Concentration in vacuo afforded the crude product which was passed through a short plug of silica gel eluting with chloroform, the eluent was concentrated and the residual triturated with hexanes affording the product as a yellow solid in 117 mg (66.0%). The residual solvent was removed in vacuo affording pure product as a yellow solid, mp 60.0- 62.9 C, [a]20D +24.0 (c 0.01, MeOH}. UV (MeOH) 396 nm (epsilon 14,455), 318 nm (epsilon 6327). NMR (CDCI3, 500 MHz): delta 15.33 (bs, IH), 8.16 (d, IH, J= 2.0Hz), 8.08 (s, 111), 7.61-6.85 (m, 9Eta), 5.22 (s, 2Eta), 4.11 (m, IH), 3.94 (m, IH), 3.78 (s, IH), 2.23 (m. III).2.10 (m, IH), 1.88 (m, IH), 1.78 (m, 211).1.59 (m, IH).13C NMR (CDCI3, 125 MHz): delta 181.3, 180.6, 163.4, 163.3, 162.4, 162.1, 162.0, 161.4, 161.3, 160.4, 160.1, 160.0, 159.2, 145.5, 143.9, 142.3, 141.6, 132.4.1 2.4.132.3, 131.5.131.4, 131.3, 131.3, 131.2, 130.7, 130.6, 125.0, 124.9, 124.8, 122.8, 122.7, 122.5, 122.2.122.2, 122.1, 122.1.117.1, 115.9, 115.7, 115.6, 111.9, 111.9, 111.8, 111.7, 104.7, 104.5, 104.3,98.3,79.5,79.3,61.0,60.6,51.5,47.7,47.3, 32.9, 32.8, 32.7, 30.8, 30.7, 30.5, 21.7, 21.5. HRMS (M+H)+ calculated mass 527.1794 for C28H26F3N2O5, found 527.1799.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 68327-04-8, (1S,2S)-2-Aminocyclopentanol hydrochloride.

Reference:
Patent; UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.; NAIR, Vasu; OKELLO, Maurice, O.; NISHONOV, Abdumalik, A.; MISHRA, Sanjaykumar; WO2011/71849; (2011); A2;,
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The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 68327-04-8, name is (1S,2S)-2-Aminocyclopentanol hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 68327-04-8

H) 6- (2-fluoro-4- ( lH-pyrazol-l-yl ) benzyl ) -2- ( (1S,2S) -2- hydroxycyclopentyl ) -4 , 5-dimethylisoindolin-l-on.e A solution of methyl 5- (2-fluoro-4- ( lH-pyrazol-1- yl) benzyl) -2-formyl-3, 4-dimethylbenzoate (0.17 g) , (lS,2S)-2- aminocyclopentanol hydrochloride (0,06 g) , triethylamine (0.06 mL) and anhydrous magnesium sulfate (0.10 g) in THF (3.40 mL) was stirred at room temperature for 10 hr. The insoluble substance was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was diluted with methanol (3.40 mL) and THF (3.40 mL) , sodium triacetoxyborohydride (0.19 g) was added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.07 g) . XH NMR (300 MHz, DMSO-d6) delta 1.45-1.60 (1H, m) , 1.62-1.79 (3H, m) , 1.80-1.98 (2H, m) , 2.24 (3H, ‘s), 2.25 (3H, s), 4.08-4.29 (4H, m),.4.39 (2H, s) , 4.88 (1H, d, J = 4.9 Hz), 6.52-6.58 (1H, m) , 7.15 (1H, t, J = 8.4 Hz), 7.23 (1H, s) , 7.63 (1H, dd, J = 8.3, 2.1 Hz), 7.68-7.77 (2H, m) , 8.52 (1H, d, J = 2.5 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 68327-04-8.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMADA, Masami; SUZUKI, Shinkichi; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; KAMATA, Makoto; WO2015/163485; (2015); A1;,
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Related Products of 68327-04-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.68327-04-8, name is (1S,2S)-2-Aminocyclopentanol hydrochloride, molecular formula is C5H12ClNO, molecular weight is 137.6079, as common compound, the synthetic route is as follows.

A solution of 128 mg intermediate 6-(4-chlorophenyl)-2-(1 -methyl-i H-pyrazol-4-yl)-3-oxo-2,3- dihydropyridazine-4-carboxylic acid (46%), 50 mg (1 S,2S)-2-aminocyclopentanol hydrochloride (1:1), 135 mg HATU, 0.13 mL ethyldiisopropylamine and 1 mg 4-dimethylaminopyridine in 1 mL of DMF was stirred at room temperature for 14 hours. Then the reaction mixture wasfiltered and subjected to RP-HPLC (instrument: Labomatic HD-3000 HPLC gradient pump, Labomatic Labocol Vario-2000 fraction collector; column: Chromatorex 0-18 125 mm x 30 mm, eluent A: 0.ivol% formic acid in water, eluent B: acetonitrile; gradient: A 70% I B 30% – A 30% I B 70%; flow: 150 mLlmin; UV-detection: 254 nm) to yield 3 mg 6-(4-chlorophenyl)-N- [(1 S ,2S)-2-hyd roxycyclopentyl]-2-(i -methyl-i H-pyrazol-4-yl)-3-oxo-2 ,3-d ihyd ropyridazine-4-carboxamide.1H NMR (400 MHz, DMSO-d6) 6 [ppm] = 1.38- 1.58 (m, 2 H), 1.60- 1.79 (m, 2 H), 1.80- 1.89(m, 1 H), 2.03 -2.18 (m, 1 H), 3.93 (s, 3 H), 3.94 – 3.99 (m, 1 H), 3.99 -4.07 (m, 1 H), 4.97 (d,1 H), 7.55 – 7.65 (m, 2 H), 8.07 – 8.14 (m, 3 H), 8.52 – 8.60 (m, 2 H), 9.44 (d, 1 H).

Statistics shows that 68327-04-8 is playing an increasingly important role. we look forward to future research findings about (1S,2S)-2-Aminocyclopentanol hydrochloride.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM; GUTCHER, Ilona; ROeHN, Ulrike; SCHMEES, Norbert; ZORN, Ludwig; ROeSE, Lars; BADER, Benjamin; KOBER, Christina; CARRETERO, Rafael; STOeCKIGT, Detlef; IRLBACHER, Horst; PLATTEN, Michael; (397 pag.)WO2018/146010; (2018); A1;,
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Application of 68327-04-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 68327-04-8, name is (1S,2S)-2-Aminocyclopentanol hydrochloride, molecular formula is C5H12ClNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 119Synthesis of (1S,2S)-2-(3-flupsilonorophenethylamino)cyclopentanol (XIII-I) trans-(1S, 2S)-2-Aminocyclopentanol hydrochloride (1.51 g, 0.011 mol) and triethylamine (Et3N, 1.32 g, 1.81 g, 0.013 mol), 3 A molecular sieves (3 g) were dissolved in dry DCE (30 mL). The mixture was stirred at room temperature under a N2 atmosphere for 10 min. NaBH(OAc)3 (2.76 g, 0.013 mol) and 1-4 (1.38 g, 0.01 mol) was then added, and the reaction mixture was stirred at room temperature under a N2 atmosphere overnight. NaOH (1 M, 20 mL) was then added, and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (20 mL x 2). The combined organic layers were washed with 1 M NaOH (20 mL) and H2O (20 mL), and then dried over Na2SO4. The solvent was concentrated in vacuo. The residue was purified by column chromatography (silica gel, CH2Cl2 : MeOH = 9.5 : 0.5) to afford a pale-yellow oil (1.38 g, 62%)

According to the analysis of related databases, 68327-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NORTHWESTERN UNIVERSITY; SILVERMAN, Richard, B.; JI, Haitao; LAWTON, Graham, R.; WO2008/42353; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 68327-04-8, (1S,2S)-2-Aminocyclopentanol hydrochloride, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Formula: C5H12ClNO, blongs to alcohols-buliding-blocks compound. Formula: C5H12ClNO

A mixture of 5,6-dimethyl-4-(4-(1-methyl-1H-pyrazol-3-yl)benzyl)picolinic acid (30.0 mg), (1S,2S)-2-aminocyclopentanol hydrochloride (19.3 mg), WSC (26.8 mg), HOBt (18.9 mg) and triethylamine (28.3 mg) in DMF (1 mL) was stirred at room temperature overnight. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution and extracted twice with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol), and solidified with ethyl acetate-hexane to give the title compound (30.0 mg). 1H NMR (300 MHz, CDCl3) delta1.60-1.96 (4H, m), 2.03-2.18 (1H, m), 2.22 (3H, s), 2.24-2.34 (1H, m), 2.53 (3H, s), 3.94 (3H, s), 3.95-4.03 (1H, m), 4.05 (2H, s), 4.08-4.18 (1H, m), 4.71 (1H, brs), 6.49 (1H, d, J = 1.7 Hz), 7.11 (2H, d, J = 8.0 Hz), 7.36 (1H, d, J = 1.9 Hz), 7.69 (2H, d, J = 8.0 Hz), 7.88 (1H, s), 8.20 (1H, brs).

The synthetic route of 68327-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 68327-04-8, (1S,2S)-2-Aminocyclopentanol hydrochloride, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, name: (1S,2S)-2-Aminocyclopentanol hydrochloride, blongs to alcohols-buliding-blocks compound. name: (1S,2S)-2-Aminocyclopentanol hydrochloride

5-Methyl-4-(4-(1-methyl-1H-pyrazol-3-yl)benzyl)picolinic acid (507 mg), (1S,2S)-2-aminocyclopentanol hydrochloride (454 mg), WSC (632 mg), HOBt (446 mg) and triethylamine (334 mg) were stirred in DMF (20 mL) under a nitrogen atmosphere at room temperature overnight. To the reaction mixture were added water and triethylamine (1 mL), and the mixture was extracted 4 times with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) and crystallized from ethyl acetate-hexane to give the title compound (537 mg). 1H NMR (300 MHz, CDCl3) delta 1.61-1.92 (4H, m), 2.04-2.16 (1H, m), 2.18-2.27 (1H, m), 2.29 (3H, s), 3.94 (3H, s), 3.96-4.02 (1H, m), 4.04 (2H, s), 4.07-4.18 (1H, m), 4.60 (1H, d, J = 1.5 Hz), 6.50 (1H, d, J = 2.3 Hz), 7.13 (2H, d, J = 8.1 Hz), 7.36 (1H, d, J = 2.3 Hz), 7.70 (2H, d, J = 8.1 Hz), 8.00 (1H, s), 8.11 (1H, d, J = 3.0 Hz), 8.28 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,68327-04-8, (1S,2S)-2-Aminocyclopentanol hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 68327-04-8, (1S,2S)-2-Aminocyclopentanol hydrochloride, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 68327-04-8, blongs to alcohols-buliding-blocks compound. name: (1S,2S)-2-Aminocyclopentanol hydrochloride

150 mg (0.56 mmol) 3-(1-benzofur-2-yl)-6-chloroimidazo[1,2-b]pyridazine and 183.7 mg (1.34 mmol) (1S,2S)-2-aminocyclopentanol hydrochloride (1:1) and 186.9 mg (2.23 mmol) sodium hydrogencarbonate in 5.0 mL butan-1-ol were stirred 72 h at 150C. The solvent was removed. The residue was purified by HPLC to yield 29 mg (16%) of the compound. LC-MS (Method 2): Rt = 0.93 min; MS (ESIpos) m/z = 335 [M+H]+. 1H-NMR (300 MHz ,DMSO-d6), delta [ppm]= 1.47-1.91 (5H), 2.18-2.32 (1H), 3.92-4.01 (1H), 4.08-4.15 (1H), 4.78-4.82 (1H), 6.73-6.79 (1H), 7.10-7.16 (1H), 7.20-7.32 (2H), 7.56-7.66 (2H), 7.74-7.82 (2H), 7.88-7.92 (1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,68327-04-8, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ZORN, Ludwig; EIS, Knut; SCHULZE, Volker; SUeLZLE, Detlev; PUeHLER, Florian; LIENAU, Philip; BOeMER, Ulf; PETERSEN, Kirstin; HAeGEBARTH, Andrea; WO2014/76162; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 68327-04-8, (1S,2S)-2-Aminocyclopentanol hydrochloride, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 68327-04-8, blongs to alcohols-buliding-blocks compound. HPLC of Formula: C5H12ClNO

To a mixture of 2- (benzoyloxy) -5-bromo-3-chloro-4- methylbenzoic acid (13.2 g) , (IS, 2S) -2-aminocyclopentanol hydrochloride (4.93 g) , triethylamine (16.5 mL) , and DMF (250 mL) was added HATU (15.0 g) at 0C, and the mixture was stirred at room temperature for 4 hr. To the reaction mixture were added ethyl acetate and water at 0C. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.36 g).MS: [M+H]+452.0,’454.0

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,68327-04-8, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; SUGIMOTO, Takahiro; SUZUKI, Shinkichi; SAKAMOTO, Hiroki; YAMADA, Masami; NAKAMURA, Minoru; KAMATA, Makoto; SHIMOKAWA, Kenichiro; OGINO, Masaki; KIMURA, Eiji; MURAKAMI, Masataka; YONEMORI, Jinichi; KOJIMA, Takuto; (281 pag.)WO2016/208775; (2016); A1;,
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Synthetic Route of 68327-04-8, Adding some certain compound to certain chemical reactions, such as: 68327-04-8, name is (1S,2S)-2-Aminocyclopentanol hydrochloride,molecular formula is C5H12ClNO, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 68327-04-8.

To a mixture of 4-bromo-l-hydroxy-2-naphthoic acid (5.00 g) , (IS, 2S) -2-aminocyclopentanol hydrochloride (2.71 g) , HATU (9.25 g) and DMF (30 mL) was added triethylamine (7.83 mL) at 0C, and the mixture was stirred at room temperature overnight. To the reaction mixture was added water, and the mixture was extracted with a mixed solvent of ethyl acetate and THF. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under, reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the titlecompound (1.69 g) .MS: [M-H]~347.9, 349.9

According to the analysis of related databases, 68327-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; SUGIMOTO, Takahiro; SUZUKI, Shinkichi; SAKAMOTO, Hiroki; YAMADA, Masami; NAKAMURA, Minoru; KAMATA, Makoto; SHIMOKAWA, Kenichiro; OGINO, Masaki; KIMURA, Eiji; MURAKAMI, Masataka; YONEMORI, Jinichi; KOJIMA, Takuto; (281 pag.)WO2016/208775; (2016); A1;,
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Reference of 68327-04-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 68327-04-8, name is (1S,2S)-2-Aminocyclopentanol hydrochloride, molecular formula is C5H12ClNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediates 10: N-[(1S,2S)-2-Hydroxycyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide Triethylamine (1.52 ml, 10.90 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (0.59 g, 4.36 mmol) and EDC (0.84 g, 4.36 mmol) were added to a solution of (1R,2S)-2-aminocyclopentan-1-ol hydrochloride (CAS number 137254-03-6; 0.50 g, 3.63 mmol) and 2-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1001401-62-2; 0.76 g, 4.00 mmol) in DCM (10 ml). The reaction was stirred at room temperature for 18 hours and then diluted with DCM (50 ml) and washed with a saturated solution of sodium bicarbonate (2×20 ml). The crude product was purified by column chromatography (silica, 0-100% ethyl acetate/petrol) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.36-1.59 (m, 3H), 1.62-1.88 (m, 3H), 3.79-3.93 (m, 1H), 3.94-4.10 (m, 1H), 4.29-4.39 (m, 1H), 7.49-7.58 (m, 1H), 7.58-7.67 (m, 2H), 7.71-7.82 (m, 2H), 8.05 (s, 2H) MS ES+: 273 Intermediates 11: N-[(1S,2S)-2-Hydroxycyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide Prepared according to the procedure for N-[(1S,2S)-2-hydroxycyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (Intermediate 10) from 2-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1001401-62-2; 531 mg, 2.81 mmol), (1S,2S)-2-aminocyclopentan-1-ol hydrochloride (CAS number 68327-04-8; 368 mg, 2.67 mmol) and DIPEA (1401 mul, 8.02 mmol) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.33-1.48 (m, 2H), 1.49-1.79 (m, 3H), 1.83-1.97 (m, 1H), 3.80-3.88 (m, 1H), 3.89-3.98 (m, 1H), 4.57-4.67 (m, 1H), 7.43-7.55 (m, 2H), 7.56-7.67 (m, 1H), 7.73-7.83 (m, 1H), 8.03 (s, 2H), 8.09-8.23 (m, 1H) MS ES+: 273

According to the analysis of related databases, 68327-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Fieldhouse, Charlotte; Glen, Angela; Maine, Stephanie; Fujimoto, Tatsuhiko; Robinson, John Stephen; US2015/232460; (2015); A1;,
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