(1S,2R,3R,5S)-2,3,6-三羟基-4,8-二氧杂双环[3.3.0]辛烷-7-酮合成路线 （共 18 条）
反应条件
1: D-(+)-glucuronic acid-γ-lactone With sodium methylate in methanol 2: acetic anhydride With perchloric acid
参考文献
Moench, Bettina; Gebert, Antje; Emmerling, Franziska; Becker, Roland; Nehls, Irene
Carbohydrate Research, 2012 , vol. 352, p. 186 - 190
反应条件
1: NaOMe / 6 h / 20 °C 2: HClO4 / 4 - 20 °C View Scheme
参考文献
Florio, Pas; Thomson, Robin J.; Von Itzstein, Mark
Carbohydrate Research, 2000 , vol. 328, # 4 p. 445 - 448
反应条件
1: sodium methylate / methanol 2: hydrogen bromide / acetic acid 3: silver carbonate / toluene / 21 h / 20 - 75 °C / Inert atmosphere View Scheme
参考文献
Moench, Bettina; Gebert, Antje; Emmerling, Franziska; Becker, Roland; Nehls, Irene
Carbohydrate Research, 2012 , vol. 352, p. 186 - 190
反应条件
1: methanol; D-(+)-glucuronic acid-γ-lactone With acetic acid; triethylamine 2: isobutyryl chloride With pyridine in dichloromethane T=40°C;
参考文献
Iddon, Lisa; Bragg, Ryan A.; Harding, John R.; Stachulski, Andrew V.
Tetrahedron, 2010 , vol. 66, # 2 p. 537 - 541
反应条件
1: NaOMe 2: pyridine 3: 82 percent / HBr / acetic acid View Scheme
参考文献
Fehlhaber, Hans-Wolfram; Snatzke, Guenther; Vlahov, Iontscho
Liebigs Annalen der Chemie, 1987 , p. 637 - 638
反应条件
1: NaOMe / 6 h / 20 °C 2: HClO4 / 4 - 20 °C 3: HBr / acetic acid / 5 °C 4: 92 percent / NaN3; TBAHS / CH2Cl2; aq. NaHCO3 / 2 h / 20 °C View Scheme
参考文献
Florio, Pas; Thomson, Robin J.; Von Itzstein, Mark
Carbohydrate Research, 2000 , vol. 328, # 4 p. 445 - 448
反应条件
1: methanol; D-(+)-glucuronic acid-γ-lactone With sodium hydroxide T=20°C; 2 h; 2: acetic anhydride With pyridine T=0 - 20°C; 3 h;
参考文献
TIBOTEC BVBA
Patent: WO2004/58787 A2, 2004 ;
Location in patent: Page 29-30 ;
反应条件
1: methanol; D-(+)-glucuronic acid-γ-lactone; sodium methylate T=20°C; 2: acetic anhydride With perchloric acid Cooling with ice;
参考文献
ACADEMIA SINICA; PRIJOVIC, Zeljko, M.; LEU, Yu-Lin; ROFFLER, Steve, R.
Patent: WO2011/66418 A1, 2011 ;
Location in patent: Page/Page column 23 ;
WO 2011/066418 A1
反应条件
1: D-(+)-glucuronic acid-γ-lactone With sodium methylate in methanol T=20°C; 3 h; Inert atmosphere; 2: acetic anhydride With pyridine T=0 - 20°C; Inert atmosphere; Overall yield = 67percent;
参考文献
Chen, Yi; Li, Yanhong; Yu, Hai; Sugiarto, Go; Thon, Vireak; Hwang, Joel; Ding, Li; Hie, Liana; Chen, Xi
Angewandte Chemie - International Edition, 2013 , vol. 52, # 45 p. 11852 - 11856
Angew. Chem., 2013 , vol. 52, # 45 p. 11852 - 11856,5
反应条件
1: D-(+)-glucuronic acid-γ-lactone; sodium methylate in methanol 2: acetic anhydride
参考文献
Yu, Henry N.; Furukawa, Jun-Ichi; Ikeda, Tsuyoshi; Wong, Chi-Huey
Organic Letters, 2004 , vol. 6, # 5 p. 723 - 726
