(R)-(-)-3-羟基十四烷酸合成路线 （共 32 条）
反应条件
sodium hydroxide; bis(cyclohexanyl)borane; dihydrogen peroxide 1) THF, 0 deg C; 2) 40-50 deg C; Yield given. Multistep reaction. Title compound not separated from byproducts;
参考文献
Pons; Kocienski
Tetrahedron Letters, 1989 , vol. 30, # 14 p. 1833 - 1836
反应条件
recombinant Bacillus subtilis cytochrome P450(BSβ) F79L mutant; dihydrogen peroxide T=37°C; pH=7; 0.0166667 h; aq. phosphate bufferEnzymatic reaction; Kinetics; ConcentrationReagent/catalyst; regioselective reaction;
参考文献
Fujishiro, Takashi; Shoji, Osami; Nagano, Shingo; Sugimoto, Hiroshi; Shiro, Yoshitsugu; Watanabe, Yoshihito
Journal of Biological Chemistry, 2011 , vol. 286, # 34 p. 29941 - 29950
反应条件
1: HCl / 2 h / Ambient temperature 2: 0.1 eq. triflic acid / CH2Cl2; cyclohexane / 10 - 20 °C 3: 1.1 eq. DiBALH / CH2Cl2 / -78 °C 4: 83 percent / BF3*Et2O / diethyl ether / 3 h / -15 - 5 °C 5: 61 percent / 1.1 eq. TBAF / tetrahydrofuran / 0.02 h / 80 °C 6: 88 percent / H2 / Pd-C / tetrahydrofuran / 8 h / Ambient temperature View Scheme
参考文献
Pons; Kocienski
Tetrahedron Letters, 1989 , vol. 30, # 14 p. 1833 - 1836
反应条件
1: HCl / 2 h / Ambient temperature 2: 0.1 eq. triflic acid / CH2Cl2; cyclohexane / 10 - 20 °C 3: 1.1 eq. DiBALH / CH2Cl2 / -78 °C 4: 83 percent / BF3*Et2O / diethyl ether / 3 h / -15 - 5 °C 5: 61 percent / 1.1 eq. TBAF / tetrahydrofuran / 0.02 h / 80 °C 6: 88 percent / H2 / Pd-C / tetrahydrofuran / 8 h / Ambient temperature 7: 73 percent / 1.2 eq. Ph3P, 1.3 eq. DEAD / tetrahydrofuran / 0 - 20 °C View Scheme
参考文献
Pons; Kocienski
Tetrahedron Letters, 1989 , vol. 30, # 14 p. 1833 - 1836
反应条件
1: HCl / 2 h / Ambient temperature 2: 0.1 eq. triflic acid / CH2Cl2; cyclohexane / 10 - 20 °C 3: 1.1 eq. DiBALH / CH2Cl2 / -78 °C 4: 83 percent / BF3*Et2O / diethyl ether / 3 h / -15 - 5 °C 5: 61 percent / 1.1 eq. TBAF / tetrahydrofuran / 0.02 h / 80 °C 6: 88 percent / H2 / Pd-C / tetrahydrofuran / 8 h / Ambient temperature View Scheme
参考文献
Pons; Kocienski
Tetrahedron Letters, 1989 , vol. 30, # 14 p. 1833 - 1836
反应条件
1: 76 percent / LiAlH4 / tetrahydrofuran / 2.5 h / Ambient temperature 2: 36.9 g / pyridine / 2 h / 60 °C 3: NaH / tetrahydrofuran / 16 h / Heating 4: p-TsOH*H2O / methanol / 0.75 h / Ambient temperature View Scheme
参考文献
Shiozaki; Kobayashi; Ishida; Arai; Hiraoka; Nishijima; Kuge; Otsuka; Akamatsu
Carbohydrate Research, 1991 , vol. 222, p. 57 - 68
反应条件
1: HCl / 2 h / Ambient temperature
2: 0.1 eq. triflic acid / CH2Cl2; cyclohexane / 10 - 20 °C
View Scheme
参考文献
Pons; Kocienski
Tetrahedron Letters, 1989 , vol. 30, # 14 p. 1833 - 1836
反应条件
1: 76 percent / LiAlH4 / tetrahydrofuran / 2.5 h / Ambient temperature
2: 36.9 g / pyridine / 2 h / 60 °C
3: NaH / tetrahydrofuran / 16 h / Heating
4: p-TsOH*H2O / methanol / 0.75 h / Ambient temperature
5: 96 percent / Et3N / CH2Cl2 / 1 h / 15 - 20 °C
View Scheme
参考文献
Shiozaki; Kobayashi; Ishida; Arai; Hiraoka; Nishijima; Kuge; Otsuka; Akamatsu
Carbohydrate Research, 1991 , vol. 222, p. 57 - 68
反应条件
hydrogenchloride
2 h; Ambient temperature; Yield given. Title compound not separated from byproducts;
参考文献
Pons; Kocienski
Tetrahedron Letters, 1989 , vol. 30, # 14 p. 1833 - 1836
反应条件
1: 36.0 g / triethylamine / ethyl acetate
2: 99 percent / hexamethyldisiloxane; TMSOTf; triethylsilane / tetrahydrofuran
3: 81 percent / AcOH; zinc-copper couple
View Scheme
参考文献
Inage, M.; Chaki, H.; Imoto, M.; Shimamoto, T.; Kusumoto, S.; Shiba, T.
Tetrahedron Letters, 1983 , vol. 24, # 19 p. 2011 - 2014
