(R)-(-)-3-羟基十四烷酸合成路线 （共 32 条）
反应条件
di-tert-butyl-4-methylphenol in tetrahydrofuran T=65°C; 3 h; Pseudomonas lipase;
参考文献
Sugai, Takeshi; Ritzen, Helena; Wong, Chi-Huey
Tetrahedron: Asymmetry, 1993 , vol. 4, # 5 p. 1051 - 1058
反应条件
1: K3Fe(CN)6; K2CO3; water / 4,6-bis(9-O-dihydroquinidinyl)-2,5-diphenylpyrimidine; OsO4 / 2-methyl-propan-2-ol; toluene / 24 h / 20 °C 2: 92 percent / pyridine; thionyl chloride / 5 h / 0 °C 3: 86 percent / dimethylformamide / 12 h / 90 °C 4: 95 percent / aq. HCl / CH2Cl2 / 12 h / 100 °C View Scheme
参考文献
Nandanan; Phukan, Prodeep; Sudalai
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999 , vol. 38, # 8 p. 893 - 896
反应条件
Porcine Pancreas Lipase; water in aq. phosphate buffer T=36°C; pH=7.6; 7 h; Resolution of racemate; enantioselective reaction;
参考文献
Kuecuek, Hatice Baspinar; Yusufoglu, Ayse
Monatshefte fur Chemie, 2013 , vol. 144, # 7 p. 1087 - 1091
反应条件
1: 1.) CuI / 1.) THF, -30 deg C, 30 min, 2.) THF, a) -30 deg C, 1 h, b) RT, overnight 2: 76 percent / aq. KOH / ethanol View Scheme
参考文献
Huang, Guangfei; Hollingsworth, Rawle I.
Tetrahedron Asymmetry, 1998 , vol. 9, # 23 p. 4113 - 4115
反应条件
1: 1.4 eq. R-Alpine-Borane / neat (no solvent) / 8 h / 0 - 20 °C 2: 1) 2.4 eq. n-BuLi; 2) 1.4 M H2SO4 / 1) THF, -78 deg C; 2) from -20 deg C to room temperature 3: 1) 2 eq. dicyclohexylborane; 2) NaOH, H2O2 / 1) THF, 0 deg C; 2) 40-50 deg C View Scheme
参考文献
Pons; Kocienski
Tetrahedron Letters, 1989 , vol. 30, # 14 p. 1833 - 1836
反应条件
1: 92 percent / pyridine; thionyl chloride / 5 h / 0 °C 2: 86 percent / dimethylformamide / 12 h / 90 °C 3: 95 percent / aq. HCl / CH2Cl2 / 12 h / 100 °C View Scheme
参考文献
Nandanan; Phukan, Prodeep; Sudalai
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999 , vol. 38, # 8 p. 893 - 896
反应条件
1: 86 percent / dimethylformamide / 12 h / 90 °C 2: 95 percent / aq. HCl / CH2Cl2 / 12 h / 100 °C View Scheme
参考文献
Nandanan; Phukan, Prodeep; Sudalai
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999 , vol. 38, # 8 p. 893 - 896
反应条件
1: 1) 2.4 eq. n-BuLi; 2) 1.4 M H2SO4 / 1) THF, -78 deg C; 2) from -20 deg C to room temperature 2: 1) 2 eq. dicyclohexylborane; 2) NaOH, H2O2 / 1) THF, 0 deg C; 2) 40-50 deg C View Scheme
参考文献
Pons; Kocienski
Tetrahedron Letters, 1989 , vol. 30, # 14 p. 1833 - 1836
反应条件
hydrogenchloride; phenol in water T=105°C; Reagent/catalyst;
参考文献
Graupner, Katharina; Scherlach, Kirstin; Bretschneider, Tom; Lackner, Gerald; Roth, Martin; Gross, Harald; Hertweck, Christian
Angewandte Chemie - International Edition, 2012 , vol. 51, # 52 p. 13173 - 13177
Angew. Chem., 2012 , vol. 124, # 52 p. 13350 - 13354,5
反应条件
in diethyl ether (saponification);
参考文献
Hiramoto; Okada; Nagai; Kawamoto
Chemical and pharmaceutical bulletin, 1971 , vol. 19, # 7 p. 1308 - 1314
