Technology Process of (-)-(S)-3-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxy-phenyl}heptanal
There total 10 articles about (-)-(S)-3-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxy-phenyl}heptanal which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
oxalyl dichloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -60 - 20 ℃;
DOI:10.1021/ja000429q
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 98 percent / Et3N; DMAP / CH2Cl2 / -20 - 20 °C
2.1: t-BuLi / ethanol; pentane / 0.5 h / -78 °C
2.2: 92 percent / ethanol; pentane / -78 - 20 °C
3.1: 70 percent / DBU; lithium chloride / acetonitrile / 36 h
4.1: 97 percent / NaBH4; CeCl3*7H2O / ethanol / 0 °C
5.1: Amano P-30 lipase; 4A molecular sieves / hexane / 12 h / 20 °C
6.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C
6.2: 80 percent / tetrahydrofuran / -78 - 20 °C
7.1: 95 percent / DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
8.1: 99 percent / hydrogen / Pd/C / ethanol
9.1: 90 percent / DMSO; oxaloyl chloride; Et3N / CH2Cl2 / -60 - 20 °C
With
dmap; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; 4 A molecular sieve; Amano P-30 lipase; hydrogen; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; acetonitrile; pentane;
1.1: sililation / 2.1: Metallation / 2.2: Formylation / 3.1: Masamune olefination / 4.1: Reduction / 5.1: enzymatic acetylation / 6.1: Metallation / 6.2: sigmatropic rearrangement / 7.1: Reduction / 8.1: Catalytic hydrogenation / 9.1: Oxidation;
DOI:10.1021/ja000429q
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 98 percent / Et3N; DMAP / CH2Cl2 / -20 - 20 °C
2.1: t-BuLi / ethanol; pentane / 0.5 h / -78 °C
2.2: 92 percent / ethanol; pentane / -78 - 20 °C
3.1: 70 percent / DBU; lithium chloride / acetonitrile / 36 h
4.1: 97 percent / NaBH4; CeCl3*7H2O / ethanol / 0 °C
5.1: Amano P-30 lipase; 4A molecular sieves / hexane / 12 h / 20 °C
6.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C
6.2: 80 percent / tetrahydrofuran / -78 - 20 °C
7.1: 95 percent / DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
8.1: 99 percent / hydrogen / Pd/C / ethanol
9.1: 90 percent / DMSO; oxaloyl chloride; Et3N / CH2Cl2 / -60 - 20 °C
With
dmap; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; 4 A molecular sieve; Amano P-30 lipase; hydrogen; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; acetonitrile; pentane;
1.1: sililation / 2.1: Metallation / 2.2: Formylation / 3.1: Masamune olefination / 4.1: Reduction / 5.1: enzymatic acetylation / 6.1: Metallation / 6.2: sigmatropic rearrangement / 7.1: Reduction / 8.1: Catalytic hydrogenation / 9.1: Oxidation;
DOI:10.1021/ja000429q
![(S)-3-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxy-phenyl}heptan-1-ol](/Databaselist/images/loading.webp)
