Technology Process of [(2E,4S,5S,7S,8Z,10S,11R,12R,14R)-5,7,11,15-tetrakis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethylpentadeca-2,8-dienyloxy]triphenylmethane
There total 31 articles about [(2E,4S,5S,7S,8Z,10S,11R,12R,14R)-5,7,11,15-tetrakis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethylpentadeca-2,8-dienyloxy]triphenylmethane which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
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871236-74-7
(2R,4R,5R,6S,7Z,11S,12S,13E)-1,9,11-tris(tert-butyldimethylsilyloxy)-2,4,6,12-tetramethyl-15-(trityloxy)pentadeca-7,13-dien-5-ol
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871236-75-8
[(2E,4S,5S,7S,8Z,10S,11R,12R,14R)-5,7,11,15-tetrakis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethylpentadeca-2,8-dienyloxy]triphenylmethane
- Guidance literature:
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With
2,6-dimethylpyridine;
In
dichloromethane;
at 0 ℃;
for 1h;
DOI:10.1016/j.tet.2007.05.033
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871236-75-8
[(2E,4S,5S,7S,8Z,10S,11R,12R,14R)-5,7,11,15-tetrakis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethylpentadeca-2,8-dienyloxy]triphenylmethane
- Guidance literature:
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Multi-step reaction with 13 steps
1.1: NaH / tetrahydrofuran; various solvent(s) / -78 - 20 °C
1.2: tetrahydrofuran; various solvent(s) / 1 h / 0 °C
1.3: 1.68 g / various solvents / -78 - 20 °C
2.1: 97 percent / diisobutylaluminum hydride / hexane; CH2Cl2 / 1 h / -78 °C
3.1: 94 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating
4.1: 82 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C
5.1: Dess-Martin periodinane / CH2Cl2 / 1 h
6.1: NaH2PO4*H2O; NaClO2; 2-methyl-2-butene / tetrahydrofuran; H2O / 2 h
7.1: 0.37 g / Et3N; 4-(dimethylamino)pyridine; DCC / CH2Cl2 / 0 - 20 °C
8.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C
8.2: 98 percent / tetrahydrofuran; hexane / -78 - 0 °C
9.1: 87 percent / i-PrOH / (S,S)-Noyori catalyst / 12 h
10.1: 90 percent / hydrogen / Lindlar catalyst / toluene / 1 h
11.1: 100 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
12.1: 84 percent / DDQ; H2O / CH2Cl2 / 1 h
13.1: 94 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
With
pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; water; hydrogen; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; dicyclohexyl-carbodiimide; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
Lindlar's catalyst; (S,S)-Noyori catalyst;
In
tetrahydrofuran; hexane; dichloromethane; water; toluene;
1.2: Wadsworth-Horner-Emmons reaction / 5.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2007.05.033
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871236-75-8
[(2E,4S,5S,7S,8Z,10S,11R,12R,14R)-5,7,11,15-tetrakis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethylpentadeca-2,8-dienyloxy]triphenylmethane
- Guidance literature:
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Multi-step reaction with 15 steps
1.1: 87 percent / LiBH4 / methanol; tetrahydrofuran
2.1: Dess-Martin periodinane
3.1: NaH / tetrahydrofuran; various solvent(s) / -78 - 20 °C
3.2: tetrahydrofuran; various solvent(s) / 1 h / 0 °C
3.3: 1.68 g / various solvents / -78 - 20 °C
4.1: 97 percent / diisobutylaluminum hydride / hexane; CH2Cl2 / 1 h / -78 °C
5.1: 94 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating
6.1: 82 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C
7.1: Dess-Martin periodinane / CH2Cl2 / 1 h
8.1: NaH2PO4*H2O; NaClO2; 2-methyl-2-butene / tetrahydrofuran; H2O / 2 h
9.1: 0.37 g / Et3N; 4-(dimethylamino)pyridine; DCC / CH2Cl2 / 0 - 20 °C
10.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C
10.2: 98 percent / tetrahydrofuran; hexane / -78 - 0 °C
11.1: 87 percent / i-PrOH / (S,S)-Noyori catalyst / 12 h
12.1: 90 percent / hydrogen / Lindlar catalyst / toluene / 1 h
13.1: 100 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
14.1: 84 percent / DDQ; H2O / CH2Cl2 / 1 h
15.1: 94 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
With
pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium borohydride; n-butyllithium; 2-methyl-but-2-ene; water; hydrogen; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; dicyclohexyl-carbodiimide; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
Lindlar's catalyst; (S,S)-Noyori catalyst;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene;
2.1: Dess-Martin oxidation / 3.2: Wadsworth-Horner-Emmons reaction / 7.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2007.05.033
