(R)-3-羟基肉豆蔻酸甲酯合成路线 （共 15 条）
反应条件
1: 78 percent / trifluoromethansulfonic acid / CH2Cl2; cyclohexane / 3.5 h / Ambient temperature 2: 82 percent / DIBAH / CH2Cl2 / 0.5 h / -78 °C 3: TiCl4 / CH2Cl2 / 1.5 h / -78 °C 4: 64 percent / KOH/MeOH / 3 h / Heating 5: 61 percent / benzenesulfonyl chloride / pyridine / 24 h / 0 °C 6: 70 percent / hydrogen / Pd/C (10percent) / tetrahydrofuran / Ambient temperature View Scheme
参考文献
Schwindt, Mark A.; Fleming, Michael P.; Han, Yeun-Kwei; Hodges, Lewis M.; Johnston, David A.; Micheli, Roger P.; Roberts, Chris R.; Snyder, Roger; Topping, Robert J.; Puentener, Kurt; Scalone, Michelangelo
Organic Process Research and Development, 2007 , vol. 11, # 3 p. 524 - 533
反应条件
1: 78 percent / trifluoromethansulfonic acid / CH2Cl2; cyclohexane / 3.5 h / Ambient temperature 2: 82 percent / DIBAH / CH2Cl2 / 0.5 h / -78 °C 3: TiCl4 / CH2Cl2 / 1.5 h / -78 °C 4: 64 percent / KOH/MeOH / 3 h / Heating 5: 61 percent / benzenesulfonyl chloride / pyridine / 24 h / 0 °C 6: 70 percent / hydrogen / Pd/C (10percent) / tetrahydrofuran / Ambient temperature 7: 77 percent / triphenylphosphine diethyl azodicarboxylate / tetrahydrofuran / 1.) 0 deg C, 1 h; 2.) room temp. 2 h View Scheme
参考文献
Schwindt, Mark A.; Fleming, Michael P.; Han, Yeun-Kwei; Hodges, Lewis M.; Johnston, David A.; Micheli, Roger P.; Roberts, Chris R.; Snyder, Roger; Topping, Robert J.; Puentener, Kurt; Scalone, Michelangelo
Organic Process Research and Development, 2007 , vol. 11, # 3 p. 524 - 533
反应条件
1: 78 percent / trifluoromethansulfonic acid / CH2Cl2; cyclohexane / 3.5 h / Ambient temperature 2: 82 percent / DIBAH / CH2Cl2 / 0.5 h / -78 °C 3: TiCl4 / CH2Cl2 / 1.5 h / -78 °C 4: 64 percent / KOH/MeOH / 3 h / Heating 5: 61 percent / benzenesulfonyl chloride / pyridine / 24 h / 0 °C 6: 70 percent / hydrogen / Pd/C (10percent) / tetrahydrofuran / Ambient temperature View Scheme
参考文献
Schwindt, Mark A.; Fleming, Michael P.; Han, Yeun-Kwei; Hodges, Lewis M.; Johnston, David A.; Micheli, Roger P.; Roberts, Chris R.; Snyder, Roger; Topping, Robert J.; Puentener, Kurt; Scalone, Michelangelo
Organic Process Research and Development, 2007 , vol. 11, # 3 p. 524 - 533
反应条件
lithium hydroxide in methanol; water 12 h;
参考文献
Bauer, Joerg; Brandenburg, Klaus; Zaehringer, Ulrich; Rademann, Joerg
Chemistry - A European Journal, 2006 , vol. 12, # 27 p. 7116 - 7124
反应条件
hydrogenchloride; sodium hydroxide in methanol; water
参考文献
Hoffmann-La Roche Inc.
Patent: US5245056 A1, 1993 ;
反应条件
1: potassium hydrogencarbonate; 4-(N,N-dimethlyamino)pyridine / water; methanol; toluene / 3.5 h / 11 °C 2: 1,1-dimethylethylmagnesium chloride / tetrahydrofuran / 22.5 h / 60 °C 3: hydrogen View Scheme
参考文献
Schwindt, Mark A.; Fleming, Michael P.; Han, Yeun-Kwei; Hodges, Lewis M.; Johnston, David A.; Micheli, Roger P.; Roberts, Chris R.; Snyder, Roger; Topping, Robert J.; Puentener, Kurt; Scalone, Michelangelo
Organic Process Research and Development, 2007 , vol. 11, # 3 p. 524 - 533
反应条件
trifluorormethanesulfonic acid in dichloromethane; cyclohexane
3.5 h; Ambient temperature;
参考文献
Barbier; Schneider; Widmer
Helvetica Chimica Acta, 1987 , vol. 70, # 5 p. 1412 - 1418
反应条件
trifluorormethanesulfonic acid in dichloromethane; cyclohexane
T=10 - 20°C; 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: Et3N / tetrahydrofuran / 17 h / 20 °C
2: trimethylsilyl triflate; triethylsilane / CH2Cl2 / 14 h / 20 °C
View Scheme
参考文献
Martin, Olivier R.; Zhou, Wei; Wu, Xinfu; Front-Deschamps, Sophie; Moutel, Stephane; Schindl, Katharina; Jeandet, Patricia; Zbaeren, Claude; Bauer, Jacques A.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 20 p. 6000 - 6014
反应条件
calcium sulfate; silver(l) oxide in benzene
6 h; Ambient temperature;
参考文献
Diolez, Christian; Sarfati, S. Robert; Szabo, Ladislas
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985 , p. 57 - 60
