Technology Process of 11-(tert-butyl-dimethyl-silanyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid 3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester
There total 24 articles about 11-(tert-butyl-dimethyl-silanyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid 3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 11 steps
1: imidazole
2: 96 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
3: 86 percent / TiCl4; DIPEA / CH2Cl2 / -78 °C
4: 96 percent / diisopropyl azodicarboxylate; PBu3 / tetrahydrofuran; toluene / 6 h / -30 °C
5: AcOH; H2O / tetrahydrofuran
6: 98 percent / MnO2 / CH2Cl2 / 2 h / 20 °C
7: 96 percent / NaClO2; aq. NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 16 h / 20 °C
8: 86 percent / diisopropyl azodicarboxylate; PPh3 / toluene / 12 h / 20 °C
9: AcOH; H2O / tetrahydrofuran
10: Dess-Martin periodinane
11: aq. NaClO2; NaH2PO4
With
1H-imidazole; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tributylphosphine; di-isopropyl azodicarboxylate; water; titanium tetrachloride; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol;
2: Dess-Martin oxidation / 4: Mitsunobu dehydration / 8: Mitsunobu esterification / 10: Dess-Martin oxidation;
DOI:10.1021/ol0630191
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: NaH
2.1: PdCl2; O2; H2O / CHCl3
2.2: NaBH4
3.1: 95 percent / Et3N / CH2Cl2 / 20 h / 0 °C
4.1: 86 percent / diisopropyl azodicarboxylate; PPh3 / toluene / 12 h / 20 °C
5.1: AcOH; H2O / tetrahydrofuran
6.1: Dess-Martin periodinane
7.1: aq. NaClO2; NaH2PO4
With
sodium chlorite; sodium dihydrogenphosphate; di-isopropyl azodicarboxylate; water; oxygen; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine; triphenylphosphine; palladium dichloride;
In
tetrahydrofuran; dichloromethane; chloroform; toluene;
4.1: Mitsunobu esterification / 6.1: Dess-Martin oxidation;
DOI:10.1021/ol0630191
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 86 percent / TiCl4; DIPEA / CH2Cl2 / -78 °C
2: 96 percent / diisopropyl azodicarboxylate; PBu3 / tetrahydrofuran; toluene / 6 h / -30 °C
3: AcOH; H2O / tetrahydrofuran
4: 98 percent / MnO2 / CH2Cl2 / 2 h / 20 °C
5: 96 percent / NaClO2; aq. NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 16 h / 20 °C
6: 86 percent / diisopropyl azodicarboxylate; PPh3 / toluene / 12 h / 20 °C
7: AcOH; H2O / tetrahydrofuran
8: Dess-Martin periodinane
9: aq. NaClO2; NaH2PO4
With
manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tributylphosphine; di-isopropyl azodicarboxylate; water; titanium tetrachloride; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol;
2: Mitsunobu dehydration / 6: Mitsunobu esterification / 8: Dess-Martin oxidation;
DOI:10.1021/ol0630191