Technology Process of 2,7,13-Pentadecatrienoic acid,
9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth
oxy]-4,6,12-trimethyl-15-(triphenylmethoxy)-, ethyl ester,
(2E,4S,5S,6S,7Z,9S,11S,12S,13E)-
There total 12 articles about 2,7,13-Pentadecatrienoic acid,
9,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)meth
oxy]-4,6,12-trimethyl-15-(triphenylmethoxy)-, ethyl ester,
(2E,4S,5S,6S,7Z,9S,11S,12S,13E)- 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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672296-39-8
(4S,5S,6S,9S,11S,12S)-9,11-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-4,6,12-trimethyl-15-trityloxypentadeca-2,7,13-trienoic acid ethyl ester
- Guidance literature:
-
diethoxyphosphoryl-acetic acid ethyl ester;
With
potassium tert-butylate;
In
tetrahydrofuran;
at -78 ℃;
for 0.5h;
C55H78O6Si2;
In
tetrahydrofuran;
at -78 - 0 ℃;
for 3h;
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-
672296-39-8
(4S,5S,6S,9S,11S,12S)-9,11-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-4,6,12-trimethyl-15-trityloxypentadeca-2,7,13-trienoic acid ethyl ester
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 1 h
2.1: NaHMDS / tetrahydrofuran / -78 - 20 °C
2.2: 75 percent / tetrahydrofuran / -78 - 20 °C
3.1: aq. KOH / ethanol; tetrahydrofuran / 6 h / Heating
4.1: Et3N / tetrahydrofuran / 0.25 h / -10 °C
4.2: 1.79 g / NaBH4 / tetrahydrofuran; H2O / 0 °C
5.1: 99 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating
6.1: 74 percent / diisobutylaluminum hydride / hexane; CH2Cl2 / -78 - 0 °C
7.1: Dess-Martin periodinane / CH2Cl2 / 1 h
8.1: potassium tert-butoxide / tetrahydrofuran / 0.5 h / -78 °C
8.2: 2.01 g / tetrahydrofuran / 3 h / -78 - 0 °C
With
pyridine; dmap; potassium hydroxide; potassium tert-butylate; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; ethanol; hexane; dichloromethane;
1.1: Dess-Martin oxidation / 2.2: Wittig coupling / 7.1: Dess-Martin oxidation / 8.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033
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672296-39-8
(4S,5S,6S,9S,11S,12S)-9,11-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-4,6,12-trimethyl-15-trityloxypentadeca-2,7,13-trienoic acid ethyl ester
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 2.96 g / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
2.1: 65 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C
3.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 1 h
4.1: NaHMDS / tetrahydrofuran / -78 - 20 °C
4.2: 75 percent / tetrahydrofuran / -78 - 20 °C
5.1: aq. KOH / ethanol; tetrahydrofuran / 6 h / Heating
6.1: Et3N / tetrahydrofuran / 0.25 h / -10 °C
6.2: 1.79 g / NaBH4 / tetrahydrofuran; H2O / 0 °C
7.1: 99 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating
8.1: 74 percent / diisobutylaluminum hydride / hexane; CH2Cl2 / -78 - 0 °C
9.1: Dess-Martin periodinane / CH2Cl2 / 1 h
10.1: potassium tert-butoxide / tetrahydrofuran / 0.5 h / -78 °C
10.2: 2.01 g / tetrahydrofuran / 3 h / -78 - 0 °C
With
pyridine; 2,6-dimethylpyridine; dmap; potassium hydroxide; potassium tert-butylate; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine;
In
tetrahydrofuran; ethanol; hexane; dichloromethane;
3.1: Dess-Martin oxidation / 4.2: Wittig coupling / 9.1: Dess-Martin oxidation / 10.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033
