Technology Process of (2Z,4Z,6S,7S,8E)-7-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,9-tetramethylundeca-2,4,8-trien-1-ol
There total 11 articles about (2Z,4Z,6S,7S,8E)-7-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,9-tetramethylundeca-2,4,8-trien-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(2Z,4Z,6S,7S,8E)-methyl 7-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,9-tetramethylundeca-2,4,8-trienoate;
With
diisobutylaluminium hydride;
In
diethyl ether; hexane; dichloromethane;
at -78 - 20 ℃;
With
sodium hydroxide;
In
diethyl ether; hexane; dichloromethane; water;
DOI:10.1021/jo901565n
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: chlorodicyclohexylborane; Me2NEt / diethyl ether; hexane / -78 - 0 °C
1.2: diethyl ether; hexane / 19 h / -78 - -22 °C
2.1: 92 percent / 2,6-lutidine / CH2Cl2 / 0.75 h / -78 - -40 °C
3.1: LiBH4 / tetrahydrofuran / 76 h / -78 - 20 °C
4.1: sodium meta-periodate / methanol; H2O / 0.67 h / 0 °C
5.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.25 h / -40 °C
5.2: tetrahydrofuran; toluene / 3 h / -78 °C
6.1: DIBAl-H / CH2Cl2; hexane / 1 h / -78 °C
7.1: MnO2 / CH2Cl2 / 20 h / 20 °C
8.1: 18-crown-6; KHMDS / tetrahydrofuran / 0.25 h / -40 °C
8.2: 87 percent / tetrahydrofuran / 6 h / -78 °C
9.1: DIBAl-H / CH2Cl2; hexane / 1 h / -78 °C
With
2,6-dimethylpyridine; manganese(IV) oxide; sodium periodate; lithium borohydride; 18-crown-6 ether; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; potassium hexamethylsilazane; diisobutylaluminium hydride;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene;
1.2: Paterson aldol reaction / 5.2: Horner-Wadsworth-Emmons olefination / 8.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja071461o
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: sodium meta-periodate / methanol; H2O / 0.67 h / 0 °C
2.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.25 h / -40 °C
2.2: tetrahydrofuran; toluene / 3 h / -78 °C
3.1: DIBAl-H / CH2Cl2; hexane / 1 h / -78 °C
4.1: MnO2 / CH2Cl2 / 20 h / 20 °C
5.1: 18-crown-6; KHMDS / tetrahydrofuran / 0.25 h / -40 °C
5.2: 87 percent / tetrahydrofuran / 6 h / -78 °C
6.1: DIBAl-H / CH2Cl2; hexane / 1 h / -78 °C
With
manganese(IV) oxide; sodium periodate; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene;
2.2: Horner-Wadsworth-Emmons olefination / 5.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja071461o
