2,3-O-异亚丙基-D-来苏糖酸-1,4-内酯合成路线 (共 17 条)
反应条件
1.1: Tf2O; pyridine / CH2Cl2 1.2: 89 percent / NaN3 / dimethylformamide 2.1: 97 percent / 4A MS / tetrahydrofuran / -78 °C 3.1: 91 percent / H2 / Pd / methanol View Scheme
参考文献
Fleet, George W.J.; Petursson, Sigthor; Campbell, Arthur L.; Mueller, Richard A.; Behling, James R.; et al.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989 , p. 665 - 666
反应条件
1: With pyridine; trifluoromethylsulfonic anhydride in dichloromethane 2: With sodium azide in N,N-dimethyl-formamide
参考文献
Bleriot, Yves; Gretzke, Dirk; Kruelle, Thomas M.; Butters, Terry D.; Dwek, Raymond A.; Nash, Robert J.; Asano, Naoki; Fleet, George W.J.
Carbohydrate Research, 2005 , vol. 340, # 18 p. 2713 - 2718
参考文献
Fleet, George W.J.; Petursson, Sigthor; Campbell, Arthur L.; Mueller, Richard A.; Behling, James R.; et al.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989 , p. 665 - 666
反应条件
sodium cyanoborohydride; periodic acid in tetrahydrofuran
参考文献
Bleriot, Yves; Gretzke, Dirk; Kruelle, Thomas M.; Butters, Terry D.; Dwek, Raymond A.; Nash, Robert J.; Asano, Naoki; Fleet, George W.J.
Carbohydrate Research, 2005 , vol. 340, # 18 p. 2713 - 2718
参考文献
G. D. Searle and Co.
Patent: US4910310 A1, 1990 ;
反应条件
hydrogenchloride; methanesulfonic acid in water
T=20°C; 73 h;
参考文献
Fan, Ao; Jaenicke, Stephan; Chuah, Gaik-Khuan
Organic and Biomolecular Chemistry, 2011 , vol. 9, # 22 p. 7720 - 7726
反应条件
acetic acid
T=28 - 29°C; Cyclization; 16.5 h;
参考文献
Godskesen, Michael; Lundt, Inge; Sotofte, Inger
Tetrahedron Asymmetry, 2000 , vol. 11, # 2 p. 567 - 579
反应条件
1: aq. HCl
2: MeSO3H / acetone / 20 h / 20 °C
3: aq. AcOH / 16.5 h / 28 - 29 °C
View Scheme
参考文献
Godskesen, Michael; Lundt, Inge; Sotofte, Inger
Tetrahedron Asymmetry, 2000 , vol. 11, # 2 p. 567 - 579
反应条件
3-chloro-benzenecarboperoxoic acid in dichloromethane
12 h; Ambient temperature;
参考文献
Rao, B. Venkateswara; Lahiri, Saswata
Journal of Carbohydrate Chemistry, 1996 , vol. 15, # 8 p. 975 - 984
反应条件
1: carbon-supported palladium-bismuth; oxygen; potassium hydroxide / water / 2 h / 50 °C / pH 9
2: hydrogenchloride; methanesulfonic acid / water / 73 h / 20 °C
View Scheme
参考文献
Fan, Ao; Jaenicke, Stephan; Chuah, Gaik-Khuan
Organic and Biomolecular Chemistry, 2011 , vol. 9, # 22 p. 7720 - 7726