(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-酮合成路线 （共 74 条）
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
→
193146-53-1(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
反应条件
camphor-10-sulfonic acid in methanol
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
→
反应条件
1.1: 88 percent / CSA / methanol 2.1: PCC 2.2: 90 percent / NaClO2 3.1: 73 percent / TBAF 4.1: 77 percent / TCBCl; DIEA; DMAP 5.1: 59 percent / HF*pyr 6.1: 65 percent / mCPBA View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
Tetrahedron Letters, 1998 , vol. 39, # 47 p. 8633 - 8636
193146-51-9(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
→
反应条件
1.1: 88 percent / CSA / methanol 2.1: PCC 2.2: 90 percent / NaClO2 3.1: 73 percent / TBAF 4.1: 77 percent / TCBCl; DIEA; DMAP 5.1: 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
193146-49-5(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
→
193146-51-9(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
反应条件
2,6-dimethylpyridine in dichloromethane
T=0°C; 3 h;
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
Journal of Organic Chemistry, 2000 , vol. 65, # 22 p. 7456 - 7467
→
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
反应条件
2,6-dimethylpyridine in dichloromethane
T=0°C; 2 h;
参考文献
Schinzer, Dieter; Bauer, Armin; Schieber, Jennifer
Chemistry - A European Journal, 1999 , vol. 5, # 9 p. 2492 - 2500
→
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
反应条件
1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C
2: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C
3: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C
4: 80 percent / PCC
5: LDA
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
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
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
反应条件
1.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C
2.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C
2.2: tetrahydrofuran / 1.5 h / -95 - -80 °C
3.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
Journal of Organic Chemistry, 2000 , vol. 65, # 22 p. 7456 - 7467
→
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
反应条件
1.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C
2.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C
3.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C
3.2: tetrahydrofuran / 1.5 h / -95 - -80 °C
4.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
Journal of Organic Chemistry, 2000 , vol. 65, # 22 p. 7456 - 7467
