(5S)-3-[(2S,13R)-2,13-二羟基-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-羟基十一烷基]四氢呋喃-2-基]四氢呋喃-2-基]十三烷基]-5-甲基-5H-呋喃-2-酮合成路线 （共 102 条）
反应条件
1: 79 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 2: 1.) BF3*OEt2 / 1.) THF, -78 deg C, 10 min, 2.) THF, 20 min 3: i-Pr2NEt / CH2Cl2 / 12 h / Ambient temperature 4: TBAF / tetrahydrofuran / 6 h / 40 °C 5: 2,6-lutidine / tetrahydrofuran / 0.33 h 6: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 7: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 62, # 17 p. 5989 - 5995
反应条件
1: i-Pr2NEt / CH2Cl2 / 12 h / Ambient temperature 2: TBAF / tetrahydrofuran / 6 h / 40 °C 3: 2,6-lutidine / tetrahydrofuran / 0.33 h 4: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 5: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 62, # 17 p. 5989 - 5995
反应条件
1: 2,6-lutidine / tetrahydrofuran / 0.33 h 2: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 3: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 62, # 17 p. 5989 - 5995
反应条件
1: TBAF / tetrahydrofuran / 6 h / 40 °C 2: 2,6-lutidine / tetrahydrofuran / 0.33 h 3: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 4: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 62, # 17 p. 5989 - 5995
反应条件
1: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 2: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 62, # 17 p. 5989 - 5995
反应条件
<b>With</b> <a href="#" onclick="return RXDsubstances(event, this, '3535002', constants.ctx, '0')">hydrogen fluoride</a> <b>in</b> <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>; <a href="#" onclick="return RXDsubstances(event, this, '741857', constants.ctx, '0')">acetonitrile</a> <br />T=20°C; 12 h; Inert atmosphere; <br />
参考文献
Sinha, Subhash C.; Chen, Zhiyong; Huang, Zheng-Zheng; Nakamaru-Ogiso, Eiko; Pietraszkiewicz, Halina; Edelstein, Matthew; Valeriote, Frederick Journal of Medicinal Chemistry, 2008 , vol. 51, # 22 p. 7045 - 7048
反应条件
<b>With</b> <a href="#" onclick="return RXDsubstances(event, this, '3764305', constants.ctx, '0')">pyridinium p-toluenesulfonate</a> <b>in</b> <a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a> <br />T=40°C; 16 h; <br />
参考文献
Marshall, James A.; Hinkle, Kevin W. Journal of Organic Chemistry, 1997 , vol. 62, # 17 p. 5989 - 5995
反应条件
<b>Multi-step reaction with 6 steps<br /> </b>1: 4 Angstroem molecular sieves; SnCl<sub>4</sub> / CH<sub>2</sub>Cl<sub>2</sub> / -40 °C<br />2: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C<br />3: 0.5 h / 20 °C<br />4: Pd(PPh<sub>3</sub>)4; water / tetrahydrofuran / 2 h / 20 °C<br />5: AgNO<sub>3</sub>/SiO<sub>2</sub> / hexane; CH<sub>2</sub>Cl<sub>2</sub> / 2 h<br />6: KCN / methanol / 0.33 h<br /> <br />
参考文献
Tinsley, Jennifer M.; Roush, William R. Journal of the American Chemical Society, 2005 , vol. 127, # 31 p. 10818 - 10819
反应条件
<b>Multi-step reaction with 7 steps<br /> </b>1: diisopropylethyl amine; DMSO; SO<sub>3</sub>*pyridine / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 0 °C<br />2: 4 Angstroem molecular sieves; SnCl<sub>4</sub> / CH<sub>2</sub>Cl<sub>2</sub> / -40 °C<br />3: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C<br />4: 0.5 h / 20 °C<br />5: Pd(PPh<sub>3</sub>)4; water / tetrahydrofuran / 2 h / 20 °C<br />6: AgNO<sub>3</sub>/SiO<sub>2</sub> / hexane; CH<sub>2</sub>Cl<sub>2</sub> / 2 h<br />7: KCN / methanol / 0.33 h<br /> <br />
参考文献
Tinsley, Jennifer M.; Roush, William R. Journal of the American Chemical Society, 2005 , vol. 127, # 31 p. 10818 - 10819
反应条件
<b>Multi-step reaction with 8 steps<br /> </b>1: Pd(OH)2; H<sub>2</sub> / tetrahydrofuran / 2 h / 20 °C<br />2: diisopropylethyl amine; DMSO; SO<sub>3</sub>*pyridine / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 0 °C<br />3: 4 Angstroem molecular sieves; SnCl<sub>4</sub> / CH<sub>2</sub>Cl<sub>2</sub> / -40 °C<br />4: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C<br />5: 0.5 h / 20 °C<br />6: Pd(PPh<sub>3</sub>)4; water / tetrahydrofuran / 2 h / 20 °C<br />7: AgNO<sub>3</sub>/SiO<sub>2</sub> / hexane; CH<sub>2</sub>Cl<sub>2</sub> / 2 h<br />8: KCN / methanol / 0.33 h<br /> <br />
参考文献
Tinsley, Jennifer M.; Roush, William R. Journal of the American Chemical Society, 2005 , vol. 127, # 31 p. 10818 - 10819
