(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸合成路线 （共 69 条）
193146-63-3(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
→
反应条件
1: 73 percent / TBAF 2: 77 percent / TCBCl; DIEA; DMAP 3: 59 percent / HF*pyr 4: 65 percent / mCPBA View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
Tetrahedron Letters, 1998 , vol. 39, # 47 p. 8633 - 8636
193146-63-3(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
→
反应条件
1: 73 percent / TBAF 2: 77 percent / TCBCl; DIEA; DMAP 3: 59 percent / HF*pyr View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
Tetrahedron Letters, 1998 , vol. 39, # 47 p. 8633 - 8636
→
193146-63-3(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
sodium chlorite; sodium dihydrogenphosphate; isobutene in tetrahydrofuran; water; tert-butyl alcohol
1 h; Ambient temperature;
参考文献
Nicolaou; Ninkovic; Sarabia; Vourloumis; He; Vallberg; Finlay; Yang
Journal of the American Chemical Society, 1997 , vol. 119, # 34 p. 7974 - 7991
→
193146-63-3(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: TiCl4; iPr2NEt / CH2Cl2 / 1 h / -78 °C
1.2: 85 percent / CH2Cl2 / -78 - 0 °C
2.1: 72 percent / 2,6-lutidine / CH2Cl2 / 3.5 h / 0 °C
3.1: 30 percent / LiOH; H2O2 / tetrahydrofuran; H2O / 84 h / 20 °C
View Scheme
参考文献
Koch, Guido; Loiseleur, Olivier; Fuentes, Daniel; Jantsch, Andrea; Altmann, Karl-Heinz
Organic Letters, 2002 , vol. 4, # 22 p. 3811 - 3814
193146-53-1(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-1-羟基-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)十七-12,16-二烯-5-酮
→
193146-63-3(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1: With pyridinium chlorochromate
2: With sodium chlorite
Further stages.;
参考文献
Taylor, Richard E.; Chen, Yue
Organic Letters, 2001 , vol. 3, # 14 p. 2221 - 2223
→
193146-63-3(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: LDA
2.1: 88 percent / CSA / methanol
3.1: PCC
3.2: 90 percent / NaClO2
View Scheme
参考文献
Taylor, Richard E.; Chen, Yue
Organic Letters, 2001 , vol. 3, # 14 p. 2221 - 2223
193146-51-9(3S,6R,7S,8S,12Z,15S,16E)-1,3,7,15-四-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)十七-12,16-二烯-5-酮
→
193146-63-3(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: 88 percent / CSA / methanol
2.1: PCC
2.2: 90 percent / NaClO2
View Scheme
参考文献
Taylor, Richard E.; Chen, Yue
Organic Letters, 2001 , vol. 3, # 14 p. 2221 - 2223
193146-49-5(3S,6R,7S,8S,12Z,15S,16E)-1,3,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-7-羟基-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)十七烷基-12,16-二烯-5-酮
→
193146-63-3(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: 88 percent / CSA / methanol
2.1: PCC
2.2: 90 percent / NaClO2
View Scheme
参考文献
Taylor, Richard E.; Chen, Yue
Organic Letters, 2001 , vol. 3, # 14 p. 2221 - 2223
→
193146-63-3(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1: With 2,6-dimethylpyridine in dichloromethane
T=0 - 5°C; 4 h;
2: With water; acetic acid in tetrahydrofuran
T=5°C; 3 h;
参考文献
Hurski; Kulinkovich
Russian Journal of Organic Chemistry, 2011 , vol. 47, # 11 p. 1653 - 1674
→
193146-63-3(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
lithium hydroxide; dihydrogen peroxide in tetrahydrofuran; water
T=20°C; 84 h;
参考文献
Koch, Guido; Loiseleur, Olivier; Fuentes, Daniel; Jantsch, Andrea; Altmann, Karl-Heinz
Organic Letters, 2002 , vol. 4, # 22 p. 3811 - 3814
