[(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-基]甲烷磺酸酯合成路线 （共 9 条）
→
3381-54-2[(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-基]甲烷磺酸酯
反应条件
triethylamine in dichloromethane T=4 - 22°C; Inert atmosphere;
参考文献
Alberti, Diego; Toppino, Antonio; Geninatti Crich, Simonetta; Meraldi, Chiara; Prandi, Cristina; Protti, Nicoletta; Bortolussi, Silva; Altieri, Saverio; Aime, Silvio; Deagostino, Annamaria
Organic and Biomolecular Chemistry, 2014 , vol. 12, # 15 p. 2457 - 2467
→
3381-54-2[(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-基]甲烷磺酸酯
反应条件
4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine in dichloromethane 1.66667 h;
参考文献
JADO TECHNOLOGIES GMBH; TECHNISCHE UNIVERSITAeT DRESDEN
Patent: WO2008/68037 A1, 2008 ;
Location in patent: Page/Page column 22 ;
1182-65-6[10,13-二甲基-17-(6-甲基庚烷-2-基)-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-3-基] 4-甲基苯磺酸酯
→
3381-54-2[(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-基]甲烷磺酸酯
反应条件
1: 92 percent / 0.1M tetraethylammonium bromide / ethanol / electrolysis at -2.1 to -2.3 V 2: 85 percent / pyridine / 12 h View Scheme
参考文献
Stouwe, Claus van der; Schaefer, Hans J.
Chemische Berichte, 1981 , vol. 114, # 3 p. 946 - 958
→
3381-54-2[(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-基]甲烷磺酸酯
反应条件
1: 92.7 percent / 0.1M tetraethylammonium bromide / ethanol / electrolysis at -2.1 to -2.3 V 2: 85 percent / pyridine / 12 h View Scheme
参考文献
Stouwe, Claus van der; Schaefer, Hans J.
Chemische Berichte, 1981 , vol. 114, # 3 p. 946 - 958
→
3381-54-2[(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-基]甲烷磺酸酯
反应条件
1: 0.1M LiBr / methanol; dioxane / 20 °C / electrolysis at -1.4 V 2: 85 percent / pyridine / 12 h View Scheme
参考文献
Stouwe, Claus van der; Schaefer, Hans J.
Chemische Berichte, 1981 , vol. 114, # 3 p. 946 - 958
3381-54-2[(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-基]甲烷磺酸酯
→
反应条件
chloro-trimethyl-silane; titanium tetrachloride in dichloromethane T=-20°C; 0.0833333 h; Inert atmosphere;
参考文献
Sun, Qi; Cai, Sutang; Peterson, Blake R.
Organic Letters, 2009 , vol. 11, # 3 p. 567 - 570
3381-54-2[(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-基]甲烷磺酸酯
→
反应条件
AlCl3, aluminium chloride; trimethylsilylazide in dichloromethane T=22°C; 1 h; Inert atmosphere;
参考文献
Organic Letters, , vol. 11, # 3 p. 567 - 570
3381-54-2[(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-基]甲烷磺酸酯
→
反应条件
in N,N,N',N',N'',N''-hexamethylphosphoric triamide 20 h; Irradiation;
参考文献
Bulletin de la Societe Chimique de France, , # 2 p. 195 - 197
3381-54-2[(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-基]甲烷磺酸酯
→
反应条件
acetone; sodium iodide
参考文献
Mc Kenna; Norymberski
Journal of the Chemical Society, 1957 , p. 3893,3899
