Production Method 1

1074-12-0

89015-27-0

Reaction Conditions

1.1 Catalysts: Copper(II) triflate ,  (S,S)-2,2′-Isopropylidenebis[4-phenyl-2-oxazoline] Solvents: Dichloromethane ;  3 h, rt
1.2 Solvents: 1,2-Dichloroethane ;  24 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Asymmetric intramolecular Cannizzaro reaction of anhydrous phenylglyoxal

Ishihara, Kazuaki; Yano, Takayuki; Fushimi, Makoto, Journal of Fluorine Chemistry, 2008, 129(10), 994-997

Production Method 2

264882-04-4

89015-27-0

Reaction Conditions

1.1 Catalysts: Copper sulfate ,  Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate ,  (4S,4′S)-2,2′-[(1S)-2,2′,3,3′-Tetrahydro-1,1′-spirobi[1H-indene]-7,7′-diyl]bis[4… Solvents: Chloroform ;  4 h, rt
1.2 Reagents: Water ;  rt → 40 °C; 15 min, 40 °C

Reference

Catalytic asymmetric reaction with water: enantioselective synthesis of α-hydroxyesters by a copper-carbenoid O-H insertion reaction

Zhu, Shou-Fei; Chen, Chao; Cai, Yan; Zhou, Qi-Lin, Angewandte Chemie, 2008, 47(5), 932-934

Production Method 3

1074-12-0

89015-27-0

Reaction Conditions

1.1 Catalysts: Copper(II) triflate ,  (S,S)-2,2′-Isopropylidenebis[4-phenyl-2-oxazoline]
1.2 Reagents: 1,2-Dichloroethane
1.3 -
1.4 Reagents: Hydrochloric acid Solvents: Water
1.5 Solvents: Dichloromethane

Reference

Efficient Lewis acid catalyzed intramolecular Cannizzaro reaction

Russell, Albert E.; Miller, Steven P.; Morken, James P., Journal of Organic Chemistry, 2000, 65(24), 8381-8383

Production Method 4

6818-08-2

89015-27-0

53439-96-6

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Water ;  17 h, pH 8, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 4

Reference

Synthesis of chiral α-aryl-α-hydroxyacetic acids: substituent effects in pig liver acetone powder (PLAP) induced enantioselective hydrolysis

Basavaiah, Deevi; Krishna, Peddinti Rama, Tetrahedron, 1995, 51(8), 2403-16

Production Method 5

31197-66-7

89015-27-0

53439-96-6

Reaction Conditions

1.1 Catalysts: Dibutylmagnesium ,  Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin, 4-hydroxy-2,6-di-9-phenanthrenyl… Solvents: Mesitylene ,  Toluene ;  10 min, rt
1.2 Reagents: Catecholborane ;  24 h, rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Enantio- and chemoselective Bronsted-acid/Mg(nBu)2 catalysed reduction of α-keto esters with catecholborane

Enders, Dieter; Stoeckel, Bianca A.; Rembiak, Andreas, Chemical Communications (Cambridge, 2014, 50(34), 4489-4491

Production Method 6

4118-51-8

89015-27-0

85806-02-6

Reaction Conditions

1.1 Catalysts: Scandium triflate ,  1799512-71-2 Solvents: Tetrahydrofuran ;  30 min, 35 °C; 35 °C → 0 °C
1.2 48 h, 0 °C

Reference

Kinetic Resolution of Racemic Mandelic Acid Esters by N,N'-Dioxide-Scandium-Complex-Catalyzed Enantiomer-Selective Acylation

Zhang, Yuheng; Liu, Xiaohua; Zhou, Lin; Wu, Wangbin; Huang, Tianyu; et al, Chemistry - A European Journal, 2014, 20(48), 15884-15890

Production Method 7

4118-51-8

89015-27-0

31197-66-7

Reaction Conditions

1.1 Catalysts: Cobalt diacetate ,  2,2′-[(1S)-[1,1′-Binaphthalene]-2,2′-diylbis[(E)-nitrilomethylidyne]]bis[phenol] Solvents: Toluene ;  10 min, rt
1.2 Catalysts: Tempo ;  5 min, rt
1.3 Reagents: Oxygen ;  9 h, 90 °C

Reference

Chiral cobalt-catalyzed enantioselective aerobic oxidation of α-hydroxy esters

Alamsetti, Santosh Kumar; Sekar, Govindasamy, Chemical Communications (Cambridge, 2010, 46(38), 7235-7237

Production Method 8

31197-66-7

89015-27-0

Reaction Conditions

1.1 Solvents: Water ;  2 h, pH 7, 30 °C

Reference

Asymmetric reduction of ketones by employing Rhodotorula sp. AS2.2241 and synthesis of the β-blocker (R)-nifenalol

Yang, Wei; Xu, Jian-He; Xie, Yan; Xu, Yi; Zhao, Gang; et al, Tetrahedron: Asymmetry, 2006, 17(12), 1769-1774

Production Method 9

1075-06-5

89015-27-0

Reaction Conditions

1.1 Catalysts: Iron(2+), bis(acetonitrile)bis[1,3-dihydro-1-[5-(trifluoromethyl)-2-pyridinyl-κN… Solvents: Dichloromethane ;  16 h, rt

Reference

Chiral-at-Iron Catalyst: Expanding the Chemical Space for Asymmetric Earth-Abundant Metal Catalysis

Hong, Yubiao; Jarrige, Lucie; Harms, Klaus; Meggers, Eric, Journal of the American Chemical Society, 2019, 141(11), 4569-4572

Production Method 10

31197-66-7

89015-27-0

Reaction Conditions

1.1 Reagents: (R)-Alpine borane

Reference

Enantioselective reduction of ketones

Itsuno, Shinichi, Organic Reactions (Hoboken, 1998, 52,

Production Method 11

89015-27-0

Reaction Conditions

1.1 Reagents: Sodium formate Catalysts: [N-[(1S,2S)-2-(Amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chlo… Solvents: Methanol ;  5 h, 40 °C

Reference

Dual Pathway for the Asymmetric Transfer Hydrogenation of α-Ketoimides to Chiral α-Hydroxy Imides or Chiral α-Hydroxy Esters

Zhao, Qiankun; Zhao, Yuxi; Liao, Hang; Cheng, Tanyu; Liu, Guohua, ChemCatChem, 2016, 8(2), 412-416

Production Method 12

31197-66-7

89015-27-0

Reaction Conditions

1.1 Reagents: (R)-Alpine borane

Reference

Selective reductions. 37. Asymmetric reduction of prochiral ketones with B-(3-pinanyl)-9-borabicyclo[3.3.1]nonane

Brown, Herbert C.; Pai, G. Ganesh, Journal of Organic Chemistry, 1985, 50(9), 1384-94

Production Method 13

4118-51-8

89015-27-0

31197-66-7

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: (OC-6-53)-[N-[[3-(1,1-Dimethylethyl)-2-(hydroxy-κO)-5-[(1H-1,2,3-triazol-5-ylmet… (polystyrene-supported) Solvents: Chloroform ;  30 h, rt

Reference

Asymmetric Aerobic Oxidation of α-Hydroxy Acid Derivatives Catalyzed by Reusable, Polystyrene-Supported Chiral N-Salicylidene Oxidovanadium tert-Leucinates

Salunke, Santosh B.; Babu, N. Seshu; Chen, Chien-Tien, Advanced Synthesis & Catalysis, 2011, 353(8), 1234-1240

Production Method 14

4118-51-8

89015-27-0

31197-66-7

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: (OC-6-53)-[N-[[3,5-Bis(1,1-dimethylethyl)-2-(hydroxy-κO)phenyl]methylene]-3-meth… Solvents: Toluene ;  19 h, rt
1.2 Reagents: Water

Reference

Chiral N-salicylidene vanadyl carboxylate-catalyzed enantioselective aerobic oxidation of α-hydroxy esters and amides

Weng, Shiue-Shien; Shen, Mei-Wen; Kao, Jun-Qi; Munot, Yogesh S.; Chen, Chien-Tien, Proceedings of the National Academy of Sciences of the United States of America, 2006, 103(10), 3522-3527

(R)-Hydroxyphenylacetic acid isopropyl ester Raw materials

• Benzeneacetic acid, a-oxo-, 1-methylethyl ester
• Methylethyl phenyldiazoacetate
• 1-Methylethyl α-(acetyloxy)benzeneacetate
• PHENYLGLYOXAL MONOHYDRATE
• Isopropyl DL-Mandelate
• 2-Oxo-2-phenylacetaldehyde

(R)-Hydroxyphenylacetic acid isopropyl ester Preparation Products

• Benzeneacetic acid, a-oxo-, 1-methylethyl ester (31197-66-7)
• (R)-Hydroxyphenylacetic acid isopropyl ester (89015-27-0)
• Isopropyl (2S)-hydroxy(phenyl)acetate (53439-96-6)
• Benzeneacetic acid, α-(acetyloxy)-, 1-methylethyl ester, (S)- (9CI) (85806-02-6)

• 1. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625
• 2. Esterase-responsive polymeric prodrug-based tumor targeting nanoparticles for improved anti-tumor performance against colon cancer?
  Gang Pan,Yi-jie Bao,Jie Xu,Tao Liu,Cheng Liu,Yan-yan Qiu,Xiao-jing Shi,Hui Yu,Ting-ting Jia,Xia Yuan,Ze-ting Yuan,Yi-jun Cao RSC Adv., 2016,6, 42109-42119
• 3. Estimating and correcting interference fringes in infrared spectra in infrared hyperspectral imaging
  Ghazal Azarfar,Ebrahim Aboualizadeh,Nicholas M. Walter,Simona Ratti,Camilla Olivieri,Alessandra Norici,Michael Nasse,Achim Kohler,Mario Giordano Analyst, 2018,143, 4674-4683
• 4. Emulsion technologies for multicellular tumour spheroid radiation assays?
  Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele Zagnoni Analyst, 2016,141, 100-110
• 5. Emerging investigators
  Polym. Chem., 2015,6, 5501-5502

• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)