(1S,2R,3S,5R)-3-(苄氧基)-2-[(苄氧基)甲基]-6-氧杂二环[3.1.0]己烷合成路线 （共 15 条）
反应条件
1: (2R,3S)-2-benzyloxymethyl-6-oxabicyclolt;3.1.0gt;hexan-3-ol With sodium hydride in tetrahydrofuran T=20°C; 1 h; 2: benzyl bromide With tetra-(n-butyl)ammonium iodide in tetrahydrofuran T=20°C; 12 h;
参考文献
Synthesis, , # 13 p. 2101 - 2109
反应条件
1.1: NaH / tetrahydrofuran / 1 h / 0 °C 1.2: tetrahydrofuran / 2 h / -40 °C 2.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C 2.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C 3.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C 4.1: NaH / tetrahydrofuran / 1 h / 20 °C 4.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C View Scheme
参考文献
Synthesis, , # 13 p. 2101 - 2109
反应条件
1.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C 1.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C 2.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C 3.1: NaH / tetrahydrofuran / 1 h / 20 °C 3.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C View Scheme
参考文献
Synthesis, , # 13 p. 2101 - 2109
反应条件
1.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C 2.1: NaH / tetrahydrofuran / 1 h / 20 °C 2.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C View Scheme
参考文献
Synthesis, , # 13 p. 2101 - 2109
反应条件
1.1: NaH / tetrahydrofuran / 1 h / 0 °C 1.2: tetrahydrofuran / 2 h / -40 °C 2.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C 2.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C 3.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C 4.1: NaH / tetrahydrofuran / 1 h / 20 °C 4.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C View Scheme
参考文献
Synthesis, , # 13 p. 2101 - 2109
反应条件
1: tetrahydrofuran / -78 - -65 °C 2: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C 3: VO(acac)2, t-BuOOH / CH2Cl2 4: NaH, Bu4NI / dimethylformamide View Scheme
参考文献
Bioorganic and Medicinal Chemistry Letters, , vol. 7, # 2 p. 127 - 132
反应条件
sodium azide; ammonium chloride in ethanol T=85°C; 22 h;
参考文献
Tran, Scott B.; Ekhato, Ihoezo V.; Rinehart, J. Kent
Journal of Labelled Compounds and Radiopharmaceuticals, 2009 , vol. 52, # 11 p. 485 - 489
反应条件
sodium azide; ammonium chloride in ethanol; water 22 h; Heating;
参考文献
Biggadike, Keith; Borthwick, Alan D.; Evans, Derek; Exall, Anne M.; Kirk, Barrie E.; et al.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988 , p. 549 - 554
反应条件
1: 60 percent / LiH / dimethylformamide / 2 h / 125 °C 2: 82 percent / TEA, DMAP / CH2Cl2 3: Dess-Martin reagent, t-BuOH / CH2Cl2 4: Zn, TiCl4 / tetrahydrofuran; CH2Cl2 5: 92 percent / aq. HCl / tetrahydrofuran; methanol / 55 °C 6: 89 percent / BCl3 / CH2Cl2 / -78 °C View Scheme
参考文献
Bisacchi; Chao; Bachard; Daris; Innaimo; Jacobs; Kocy; Lapointe; Martel; Merchant; Slusarchyk; Sundeen; Young; Colonno; Zahler
Bioorganic and Medicinal Chemistry Letters, 1997 , vol. 7, # 2 p. 127 - 132
反应条件
1: 60 percent / LiH / dimethylformamide / 2 h / 125 °C 2: 82 percent / TEA, DMAP / CH2Cl2 3: Dess-Martin reagent, t-BuOH / CH2Cl2 View Scheme
参考文献
Bisacchi; Chao; Bachard; Daris; Innaimo; Jacobs; Kocy; Lapointe; Martel; Merchant; Slusarchyk; Sundeen; Young; Colonno; Zahler
Bioorganic and Medicinal Chemistry Letters, 1997 , vol. 7, # 2 p. 127 - 132
