Technology Process of (10S,11R)-11-benzoyloxy-10-(1,1-dimethylethyl)dimethylsiloxy-2,4,6,8-dodecatetraenal
There total 12 articles about (10S,11R)-11-benzoyloxy-10-(1,1-dimethylethyl)dimethylsiloxy-2,4,6,8-dodecatetraenal which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 870 mg / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
2.1: 450 mg / PPTS / methanol / 24 h
3.1: 94 percent / Dess-Martin periodinane; NaHCO3 / 1 h
4.1: n-BuLi; MgBr2 / tetrahydrofuran / -78 °C
4.2: tetrahydrofuran / 1 h / -78 °C
5.1: mesyl chloride; Et3N / CH2Cl2 / 0.75 h / -40 °C
5.2: 135 mg / tetrahydrofuran; various solvent(s) / 0.75 h / pH 7
6.1: n-BuLi; MgBr2 / tetrahydrofuran / -78 °C
6.2: tetrahydrofuran / 0.08 h / -78 °C
7.1: mesyl chloride; Et3N / CH2Cl2 / 0.17 h / -40 °C
7.2: 120 mg / tetrahydrofuran; various solvent(s) / 0.17 h / 0 °C / pH 7
With
2,6-dimethylpyridine; n-butyllithium; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; magnesium bromide;
In
tetrahydrofuran; methanol; dichloromethane;
1.1: Substitution / 2.1: Desilylation / 3.1: Oxidation / 4.1: Metallation / 4.2: Grignard reaction / 5.1: Substitution / 5.2: Hydrolysis / 6.1: Metallation / 6.2: Grignard reaction / 7.1: Substitution / 7.2: Hydrolysis;
DOI:10.1016/S0040-4020(99)00457-3
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 240 mg / CSA / methanol / 16 h
2.1: 870 mg / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
3.1: 450 mg / PPTS / methanol / 24 h
4.1: 94 percent / Dess-Martin periodinane; NaHCO3 / 1 h
5.1: n-BuLi; MgBr2 / tetrahydrofuran / -78 °C
5.2: tetrahydrofuran / 1 h / -78 °C
6.1: mesyl chloride; Et3N / CH2Cl2 / 0.75 h / -40 °C
6.2: 135 mg / tetrahydrofuran; various solvent(s) / 0.75 h / pH 7
7.1: n-BuLi; MgBr2 / tetrahydrofuran / -78 °C
7.2: tetrahydrofuran / 0.08 h / -78 °C
8.1: mesyl chloride; Et3N / CH2Cl2 / 0.17 h / -40 °C
8.2: 120 mg / tetrahydrofuran; various solvent(s) / 0.17 h / 0 °C / pH 7
With
2,6-dimethylpyridine; n-butyllithium; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; magnesium bromide;
In
tetrahydrofuran; methanol; dichloromethane;
1.1: Hydrolysis / 2.1: Substitution / 3.1: Desilylation / 4.1: Oxidation / 5.1: Metallation / 5.2: Grignard reaction / 6.1: Substitution / 6.2: Hydrolysis / 7.1: Metallation / 7.2: Grignard reaction / 8.1: Substitution / 8.2: Hydrolysis;
DOI:10.1016/S0040-4020(99)00457-3
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 450 mg / PPTS / methanol / 24 h
2.1: 94 percent / Dess-Martin periodinane; NaHCO3 / 1 h
3.1: n-BuLi; MgBr2 / tetrahydrofuran / -78 °C
3.2: tetrahydrofuran / 1 h / -78 °C
4.1: mesyl chloride; Et3N / CH2Cl2 / 0.75 h / -40 °C
4.2: 135 mg / tetrahydrofuran; various solvent(s) / 0.75 h / pH 7
5.1: n-BuLi; MgBr2 / tetrahydrofuran / -78 °C
5.2: tetrahydrofuran / 0.08 h / -78 °C
6.1: mesyl chloride; Et3N / CH2Cl2 / 0.17 h / -40 °C
6.2: 120 mg / tetrahydrofuran; various solvent(s) / 0.17 h / 0 °C / pH 7
With
n-butyllithium; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; magnesium bromide;
In
tetrahydrofuran; methanol; dichloromethane;
1.1: Desilylation / 2.1: Oxidation / 3.1: Metallation / 3.2: Grignard reaction / 4.1: Substitution / 4.2: Hydrolysis / 5.1: Metallation / 5.2: Grignard reaction / 6.1: Substitution / 6.2: Hydrolysis;
DOI:10.1016/S0040-4020(99)00457-3
