(+)-(2S,6Z,9S,10E)-9-{[叔-丁基(二甲基)硅烷基]氧基}-2,6,10-三甲基-11-(2-甲基-1,3-噻唑-4-基)-十一碳-6,10-二烯-1-醇合成路线 （共 7 条）
→
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
1.1: 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 4.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
Tetrahedron Letters, 1998 , vol. 39, # 47 p. 8633 - 8636
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 4.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 5.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 6.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 7.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 8.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 9.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C 10.1: m-CPBA / CHCl3 / 5 h / -18 °C View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
Tetrahedron Letters, 1998 , vol. 39, # 47 p. 8633 - 8636
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 4.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 5.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 6.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 7.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 8.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 9.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme
参考文献
Hurski; Kulinkovich
Russian Journal of Organic Chemistry, 2011 , vol. 47, # 11 p. 1653 - 1674
→
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
Nicolaou; Hepworth, David; Finlay, M. Ray V.; King, N. Paul; Werschkun, Barbara; Bigot, Antony
Chemical Communications, 1999 , # 6 p. 519 - 520
→
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: 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
4.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C
5.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C
6.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h
View Scheme
参考文献
Hurski; Kulinkovich
Russian Journal of Organic Chemistry, 2011 , vol. 47, # 11 p. 1653 - 1674
→
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
Tetrahedron Letters, 1998 , vol. 39, # 47 p. 8633 - 8636
反应条件
Multi-step reaction with 7 steps 1.1: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - 20 °C2.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h2.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C3.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C4.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C5.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C5.2: 93 percent / tetrahydrofuran / 1 h / -78 °C6.1: 65 percent / Na2HPO4; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C7.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth Journal of Organic Chemistry, 2000 , vol. 65, # 22 p. 7456 - 7467
