(+)-甲基(3S)-5-{[叔-丁基二甲基硅烷基)氧基]}-3-羟基-2,2-二甲基戊酸酯 合成路线 （共 11 条）
反应条件
1: 3-(t-butyl-dimethyl-silanyloxy)-propionaldehyde With borane-THF; Nα-(4-methylbenzenesulfonyl)-D-phenylalanine in dichloromethane T=-94°C; 0.25 h; 2: [(1-methoxy-2-methyl-1-propenyl)oxy]trimethylsilane in dichloromethane T=-94 - -78°C; 1.75 h; 3: With Amberlite IRA-743 in dichloromethane; water T=-78 - 20°C; 6 h;
参考文献
Storer, R. Ian; Takemoto, Toshiyasu; Jackson, Philip S.; Ley, Steven V.
反应条件
1.1: O3 / CH2Cl2 / 0.17 h / -78 °C 1.2: 93 percent / polymer-supported triphenylphosphine / CH2Cl2 / 14 h / 20 °C 2.1: N-tosyl-D-phenylalanine; BH3*THF / tetrahydrofuran; CH2Cl2 / 1.5 h / -96 - -78 °C View Scheme
参考文献
Storer, R. Ian; Takemoto, Toshiyasu; Jackson, Philip S.; Ley, Steven V.
反应条件
1.1: 96 percent / polystyrene-DMAP / CH2Cl2 / 2.5 h / 20 °C 2.1: O3 / CH2Cl2 / 0.33 h / -78 °C 2.2: 93 percent / polystyrene-PPh2 / CH2Cl2 / 12 h / -78 - 20 °C 3.1: N-Ts-D-phenylalanine; BH3*THF / CH2Cl2 / 0.25 h / -94 °C 3.2: CH2Cl2 / 1.75 h / -94 - -78 °C 3.3: 93 percent / Amberlite IRA-743 / CH2Cl2; H2O / 6 h / -78 - 20 °C View Scheme
参考文献
Storer, R. Ian; Takemoto, Toshiyasu; Jackson, Philip S.; Brown, Dearg S.; Baxendale, Ian R.; Ley, Steven V.
反应条件
1: 87 percent / pyridinium chlorochromate/basic alumina / CH2Cl2 / 1 h / 20 °C 2: N-tosyl-D-phenylalanine; BH3*THF / tetrahydrofuran; CH2Cl2 / 1.5 h / -96 - -78 °C View Scheme
参考文献
Storer, R. Ian; Takemoto, Toshiyasu; Jackson, Philip S.; Brown, Dearg S.; Baxendale, Ian R.; Ley, Steven V.
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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: 96 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 2.1: pentane / 4 h / 0 °C 2.2: 97 percent / MeOH / 1 h / 20 °C 3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C 4.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 4.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 5.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 6.1: 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: 96 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 2.1: pentane / 4 h / 0 °C 2.2: 97 percent / MeOH / 1 h / 20 °C 3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C 4.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 4.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 5.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 6.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 7.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 8.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 9.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 10.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 11.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C 12.1: 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: 96 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 2.1: pentane / 4 h / 0 °C 2.2: 97 percent / MeOH / 1 h / 20 °C 3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C 4.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 4.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 5.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 6.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 7.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 8.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 9.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 10.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 11.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme
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: 96 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
2.1: pentane / 4 h / 0 °C
2.2: 97 percent / MeOH / 1 h / 20 °C
3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C
3.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C
4.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C
4.2: tetrahydrofuran / 1.5 h / -95 - -80 °C
5.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
→
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: 96 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
2.1: pentane / 4 h / 0 °C
2.2: 97 percent / MeOH / 1 h / 20 °C
3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C
3.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C
4.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C
4.2: tetrahydrofuran / 1.5 h / -95 - -80 °C
5.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
6.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C
7.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C
8.1: 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
→
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: 96 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
2.1: pentane / 4 h / 0 °C
2.2: 97 percent / MeOH / 1 h / 20 °C
3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C
3.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C
4.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C
4.2: tetrahydrofuran / 1.5 h / -95 - -80 °C
View Scheme
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
