Production Method 1

2039-85-2

80051-04-3

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide ,  Bis(pinacolato)diborane Catalysts: (OC-6-14)-Bis(acetato-κO)aqua[2,6-bis[(4S)-4,5-dihydro-4-(1-methylethyl)-2-oxazo… Solvents: Tetrahydrofuran ;  1 h, 60 °C
1.2 Reagents: Sodium peroxoborate Solvents: Tetrahydrofuran ,  Water ;  1 h, rt

Reference

Asymmetric Diboration of Terminal Alkenes with Rhodium Catalyst and Subsequent Oxidation: Enantioselective Synthesis of Optically Active 1,2-Diols

Toribatake, Kenji; Nishiyama, Hisao, Angewandte Chemie, 2013, 52(42), 11011-11015

Production Method 2

2039-85-2

80051-04-3

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Potassium ferricyanide Catalysts: Osmium (Binaphthyl-stabilized nanoparticle) ,  1,4-Bis(9-O-dihydroquinidinyl)phthalazine ,  [1,1′-Binaphthalene]-2,2′-bis(diazonium), tetrafluoroborate(1-) (1:2) (reduction product with OsCl3) Solvents: tert-Butanol ,  Water ;  6 h, rt

Reference

Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-O-dihydroquinidinyl)phthalazine-Modified Binaphthyl-Osmium Nanoparticles

Zhu, Jie; Sun, Xiao-Tao; Wang, Xiao-Dong; Wu, Lei, ChemCatChem, 2018, 10(8), 1788-1792

Production Method 3

67829-05-4

80051-04-3

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: [N-[(1S,2S)-2-(Amino-κN)-1,2-diphenylethyl]methanesulfonamidato-κN][(1,2,3,4,5-η… Solvents: Methanol ;  15 h, 10 atm, 60 °C; 10 atm → 1 atm

Reference

Asymmetric Hydrogenation of α-Hydroxy Ketones Catalyzed by MsDPEN-CpIr(III) Complex

Ohkuma, Takeshi; Utsumi, Noriyuki; Watanabe, Masahito; Tsutsumi, Kunihiko; Arai, Noriyoshi; et al, Organic Letters, 2007, 9(13), 2565-2567

Production Method 4

20697-04-5

80051-04-3

Reaction Conditions

1.1 Reagents: Water Catalysts: Epoxide hydrolase Solvents: Water

Reference

Enantioconvergent Hydrolysis of Styrene Epoxides by Newly Discovered Epoxide Hydrolases in Mung Bean

Xu, Wei; Xu, Jian-He; Pan, Jiang; Gu, Qing; Wu, Xin-Yan, Organic Letters, 2006, 8(8), 1737-1740

Production Method 5

41904-39-6

80051-04-3

Reaction Conditions

1.1 Reagents: Diisopropylethylamine ,  3-(2-Chlorophenyl)-2-[(4-methylphenyl)sulfonyl]oxaziridine Catalysts: (9S)-6′-Methoxy-9-[(trimethylsilyl)oxy]cinchonan Solvents: Tetrahydrofuran ;  5 h, -78 °C; 19 h, -78 °C
1.2 Reagents: Ethyl acetate
1.3 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  overnight, 0 °C
1.4 Reagents: Hydrochloric acid Solvents: Methanol

Reference

Enantioselective synthesis of terminal 1,2-diols from acyl chlorides

Shao, Panlin; Shen, Litao; Ye, Song, Chinese Journal of Chemistry, 2012, 30(11), 2688-2692

Production Method 6

20697-04-5

80051-04-3

Reaction Conditions

1.1 Catalysts: Epoxide hydrolase Solvents: Ethanol

Reference

Enantioselective hydrolysis of substituted phenyloxiranes by rabbit liver microsomal epoxide hydrolase

Bellucci, G.; Chiappe, C.; Marioni, F., Indian Journal of Chemistry, 1992, (12), 828-31

Production Method 7

2039-85-2

80051-04-3

Reaction Conditions

1.1 Reagents: Sodium pyruvate ,  Oxygen Catalysts: Naphthalene 1,2-dioxygenase Solvents: Ethanol ,  Water ;  24 h, pH 7.2, 30 °C

Reference

Biocatalytic asymmetric dihydroxylation of conjugated mono- and poly-alkenes to yield enantiopure cyclic cis-diols

Boyd, Derek R.; Sharma, Narain D.; Bowers, Nigel I.; Brannigan, Ian N.; Groocock, Melanie R.; et al, Advanced Synthesis & Catalysis, 2005, 347, 1081-1089

Production Method 8

2039-85-2

80051-04-3

Reaction Conditions

1.1 Reagents: AD-mix-β Solvents: tert-Butanol ,  Water

Reference

Asymmetric dihydroxylation of alkenes

Noe, Mark C.; Letavic, Michael A.; Snow, Sheri L., Organic Reactions (Hoboken, 2005, 66,

Production Method 9

2039-85-2

80051-04-3

Reaction Conditions

1.1 Reagents: Hydrogen peroxide Catalysts: 1975976-02-3 Solvents: Methanol ;  1.5 h, 27 °C

Reference

Highly Enantioselective Iron-Catalyzed cis-Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an FeIII-OOH Reactive Intermediate

Zang, Chao; Liu, Yungen; Xu, Zhen-Jiang; Tse, Chun-Wai; Guan, Xiangguo; et al, Angewandte Chemie, 2016, 55(35), 10253-10257

Production Method 10

2039-85-2

80051-04-3

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Epoxide hydrolase ,  Styrene monooxygenase Solvents: Hexadecane ,  Water ;  8 h, pH 8, 30 °C

Reference

Enantioselective trans-Dihydroxylation of Aryl Olefins by Cascade Biocatalysis with Recombinant Escherichia coli Coexpressing Monooxygenase and Epoxide Hydrolase

Wu, Shuke; Chen, Yongzheng; Xu, Yi; Li, Aitao; Xu, Qisong; et al, ACS Catalysis, 2014, 4(2), 409-420

Production Method 11

20697-04-5

80051-04-3

Reaction Conditions

1.1 Catalysts: Epoxide hydrolase Solvents: Water ;  8 h, pH 7, 25 °C

Reference

Manipulating regioselectivity of an epoxide hydrolase for single enzymatic synthesis of (R)-1,2-diols from racemic epoxides

Hu, Die; Zong, Xun-Cheng; Xue, Feng; Li, Chuang; Hu, Bo-Chun; et al, Chemical Communications (Cambridge, 2020, 56(18), 2799-2802

Production Method 12

2039-85-2

80051-04-3

Reaction Conditions

1.1 Reagents: N-methylmorpholine N-oxide Catalysts: Osmium tetroxide ,  Cinchonanium, 6′-methoxy-9-[[4-[[(9S)-6′-methoxycinchonan-9-yl]oxy]-1-phthalazin… Solvents: tert-Butanol ,  Water ;  0.25 h, 20 °C; 20 h, 20 °C

Reference

New mono-quaternized bis-cinchona alkaloid ligands for asymmetric dihydroxylation of olefins in aqueous medium: unprecedented high enantioselectivity and recyclability

Choi, Doo Seung; Han, Sang Seop; Kwueon, Eun Kyung; Choi, Han Young; Hwang, Soon Ho; et al, Advanced Synthesis & Catalysis, 2006, 348(18), 2560-2564

Production Method 13

67829-05-4

80051-04-3

Reaction Conditions

1.1 Solvents: Water ;  28 h, pH 7.2, 32 °C

Reference

Asymmetric reduction of α-hydroxy aromatic ketones to chiral aryl vicinal diols using carrot enzymes system

Liu, Xiang; Wang, Yi; Gao, Hai Yan; Xu, Jian He, Chinese Chemical Letters, 2012, 23(6), 635-638

Production Method 14

67829-05-4

80051-04-3

Reaction Conditions

1.1 Solvents: Water ;  28 h, pH 7.0, 32 °C

Reference

Asymmetric reduction of α-hydroxy aromatic ketones to chiral aryl vicinal diols using carrot enzymatic system

Liu, Xiang; Wang, Yi; Xu, Jian He, AIChE Annual Meeting, 2011, 132,

(R)-1-(3-Chlorophenyl)-1,2-ethanediol Raw materials

• 2-(3-Chlorophenyl)acetyl Chloride
• 2-(3-Chlorophenyl)oxirane
• 3-Chlorostyrene
• Ethanone, 1-(3-chlorophenyl)-2-hydroxy-

(R)-1-(3-Chlorophenyl)-1,2-ethanediol Preparation Products

• (R)-1-(3-Chlorophenyl)-1,2-ethanediol (80051-04-3)

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• 6939-95-3(1-(3-Chlorophenyl)ethanol)
• 152142-03-5((1R)-1-(4-chlorophenyl)-1,2-ethanediol)
• 147254-28-2(1,2-Ethanediol, 1-(4-chlorophenyl)-, (1S)-)
• 842140-72-1((3-chlorophenyl)(m-tolyl)methanol)
• 63012-03-3((3-Chlorophenyl)(phenyl)methanol)
• 7477-64-7(1-(4-Chlorophenyl)ethane-1,2-diol)
• 1475-11-2(1-(3,4-Dichlorophenyl)ethanol)
• 8002-65-1(Neem Oil)
• 135145-34-5((S)-1-(3-Chlorophenyl)ethanol)
• 120121-01-9((R)-1-(3-Chlorophenyl)ethanol)