Technology Process of (S,E)-3-(4-methoxybenzyloxy)-3-methyl-9-((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)non-6-en-1-ol
There total 12 articles about (S,E)-3-(4-methoxybenzyloxy)-3-methyl-9-((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)non-6-en-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
C25H38O5;
With
mercury(II) diacetate;
In
tetrahydrofuran; water;
for 1h;
cooling;
With
sodium tetrahydroborate;
In
tetrahydrofuran; water;
for 2h;
Further stages.;
DOI:10.1021/jo062513f
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 36.0 g / (DHQ)2PHAL; K3[Fe(CN)6]; K2CO3 / K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 48 h / 0 °C
2.1: PPTS / CH2Cl2 / 1.5 h / 20 °C
3.1: 21.77 g / TBAF / tetrahydrofuran / 2 h / cooling
4.1: 59 percent / Ph3P; DIAD / tetrahydrofuran / 24 h / 20 °C
5.1: 60 percent / MCPBA / CH2Cl2 / 16 h / 20 °C
6.1: 84 percent / KHMDS / 1,2-dimethoxy-ethane; toluene / 2.5 h / -78 - 20 °C
7.1: 90 percent / DIBAL-H / CH2Cl2 / 1.5 h / -78 °C
8.1: 96 percent / Dess-Martin periodinane; pyridine / CH2Cl2; H2O / 3 h / 20 °C
9.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C
9.2: 99 percent / tetrahydrofuran / 1 h / -78 °C
10.1: Hg(OAc)2 / tetrahydrofuran; H2O / 1 h / cooling
10.2: 72 percent / NaBH4 / tetrahydrofuran; H2O / 2 h
With
pyridine; Hydroquinone 1,4-phthalazinediyl diether; di-isopropyl azodicarboxylate; mercury(II) diacetate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium hexacyanoferrate(III);
potassium dioxotetrahydroxoosmate(VI);
In
tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; toluene; tert-butyl alcohol;
4.1: Mitsunobu reaction / 6.1: Julia-Kocienski coupling / 8.1: Dess-Martin oxidation / 9.2: Wittig olefination;
DOI:10.1021/jo062513f
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: DMAP; triethylamine / CH2Cl2 / 0 - 20 °C
2.1: 36.0 g / (DHQ)2PHAL; K3[Fe(CN)6]; K2CO3 / K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 48 h / 0 °C
3.1: PPTS / CH2Cl2 / 1.5 h / 20 °C
4.1: 21.77 g / TBAF / tetrahydrofuran / 2 h / cooling
5.1: 59 percent / Ph3P; DIAD / tetrahydrofuran / 24 h / 20 °C
6.1: 60 percent / MCPBA / CH2Cl2 / 16 h / 20 °C
7.1: 84 percent / KHMDS / 1,2-dimethoxy-ethane; toluene / 2.5 h / -78 - 20 °C
8.1: 90 percent / DIBAL-H / CH2Cl2 / 1.5 h / -78 °C
9.1: 96 percent / Dess-Martin periodinane; pyridine / CH2Cl2; H2O / 3 h / 20 °C
10.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C
10.2: 99 percent / tetrahydrofuran / 1 h / -78 °C
11.1: Hg(OAc)2 / tetrahydrofuran; H2O / 1 h / cooling
11.2: 72 percent / NaBH4 / tetrahydrofuran; H2O / 2 h
With
pyridine; dmap; Hydroquinone 1,4-phthalazinediyl diether; di-isopropyl azodicarboxylate; mercury(II) diacetate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium hexacyanoferrate(III);
potassium dioxotetrahydroxoosmate(VI);
In
tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; toluene; tert-butyl alcohol;
5.1: Mitsunobu reaction / 7.1: Julia-Kocienski coupling / 9.1: Dess-Martin oxidation / 10.2: Wittig olefination;
DOI:10.1021/jo062513f
