(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-酮合成路线 （共 61 条）
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
→
193146-53-1(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
1: 88 percent / CSA / methanol 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
→
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
193146-49-5(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
→
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
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
→
193146-49-5(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
反应条件
1.1: OsO4
1.2: 80 percent / NaIO4
2.1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C
3.1: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C
4.1: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C
5.1: 80 percent / PCC
6.1: LDA
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
反应条件
1.1: OsO4
1.2: 80 percent / NaIO4
2.1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C
3.1: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C
4.1: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C
5.1: 80 percent / PCC
6.1: LDA
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
反应条件
1.1: OsO4
1.2: 80 percent / NaIO4
2.1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C
3.1: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C
4.1: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C
5.1: 80 percent / PCC
6.1: LDA
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
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
View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
Journal of Organic Chemistry, 2000 , vol. 65, # 22 p. 7456 - 7467
→
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
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
View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
Journal of Organic Chemistry, 2000 , vol. 65, # 22 p. 7456 - 7467
→
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
反应条件
1: 90 percent / DIBAL / CH2Cl2 / 1 h / -78 °C
2: 98 percent / benzene / 2 h / Heating
3: 74 percent / diethyl ether; pentane / 1 h / -100 °C
4: 99 percent / imidazole / dimethylformamide / 1) 0 deg C, 45 min, 2) 25 deg C, 2.5 h
5: 95 percent / 4-methylmorpholine N-oxide, OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 1) 0 deg C, 2.5 h, 2) 25 deg C, 12 h
6: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C
7: 95 percent / benzene / 3 h / Heating
8: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C
9: 83 percent / Ph3P, CCl4 / 24 h / 100 °C
10: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C
11: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C
12: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C
13: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h
14: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C
15: 82 percent / DIBAL / toluene / 1 h / -78 °C
16: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min
View Scheme
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
