(-)-甲基(3S)-3,5-二-{[叔-丁基二甲基硅烷基)氧基]}-2,2-二甲基戊酸酯 合成路线 （共 9 条）
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反应条件
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: pentane / 4 h / 0 °C 1.2: 97 percent / MeOH / 1 h / 20 °C 2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °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 5.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
反应条件
1.1: pentane / 4 h / 0 °C 1.2: 97 percent / MeOH / 1 h / 20 °C 2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °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 5.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 6.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 7.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 8.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 9.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 10.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C 11.1: m-CPBA / CHCl3 / 5 h / -18 °C View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
反应条件
1.1: pentane / 4 h / 0 °C 1.2: 97 percent / MeOH / 1 h / 20 °C 2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °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 5.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 6.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 7.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 8.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 9.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 10.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
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 +
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反应条件
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; Yield given;
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
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反应条件
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: pentane / 4 h / 0 °C
1.2: 97 percent / MeOH / 1 h / 20 °C
2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °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
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反应条件
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: pentane / 4 h / 0 °C
1.2: 97 percent / MeOH / 1 h / 20 °C
2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °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
5.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C
6.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C
7.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h
View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
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反应条件
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: pentane / 4 h / 0 °C
1.2: 97 percent / MeOH / 1 h / 20 °C
2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °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
反应条件
1.1: 100 percent / pentane / 3.5 h / 0 °C
2.1: LDA / hexane; tetrahydrofuran / 0.17 h / -78 - -15 °C
2.2: 94 percent / hexane; tetrahydrofuran / 2 h / -78 - -40 °C
View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
反应条件
1: PhSO2Et With n-butyllithium in tetrahydrofuran
T=-78°C; 1.5 h;
2: (-)-methyl (3S)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpentanoate in tetrahydrofuran
T=-78 - 20°C; Further stages;
参考文献
Reiff, Emily A.; Nair, Sajiv K.; Henri, John T.; Greiner, Jack F.; Reddy, Bollu S.; Chakrasali, Ramappa; David, Sunil A.; Chiu, Ting-Lan; Amin, Elizabeth A.; Himes, Richard H.; Vander Velde, David G.; Georg, Gunda I.
