Technology Process of (4E,6Z,10E,12R,14S)-12-methoxy-4,7-dimethyl-14-(trityloxymethyl)oxacyclotetradeca-4,6,10-trien-2-one
There total 19 articles about (4E,6Z,10E,12R,14S)-12-methoxy-4,7-dimethyl-14-(trityloxymethyl)oxacyclotetradeca-4,6,10-trien-2-one 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:
- Guidance literature:
-
(2Z,5Z,9E,11R,13S)-13-hydroxy-11-methoxy-3,6-dimethyl-14-(trityloxy)tetradeca-2,5,9-trienoic acid;
With
2,4,6-trichlorobenzoyl chloride; triethylamine;
In
tetrahydrofuran;
at 20 ℃;
for 1h;
Inert atmosphere;
With
dmap;
In
tetrahydrofuran; toluene;
for 12h;
Inert atmosphere;
Reflux;
DOI:10.1016/j.tetasy.2013.07.002
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 1 h / 20 °C / Inert atmosphere
2.1: (R)-10-camphorsulfonic acid / methanol / 4 h / 20 °C / Inert atmosphere
3.1: pyridine / dichloromethane / 4 h / 0 °C / Inert atmosphere
4.1: 1H-imidazole / dichloromethane / 5 h / 20 °C / Inert atmosphere
5.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -15 °C / Inert atmosphere
6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere
7.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 0.5 h / 20 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C / Inert atmosphere
9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
9.2: 12 h / Inert atmosphere; Reflux
With
pyridine; 1H-imidazole; sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; (R)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol;
6.1: |Dess-Martin Oxidation / 9.1: |Yamaguchi Lactonization;
DOI:10.1016/j.tetasy.2013.07.002
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: (R)-10-camphorsulfonic acid / methanol / 4 h / 20 °C / Inert atmosphere
2.1: pyridine / dichloromethane / 4 h / 0 °C / Inert atmosphere
3.1: 1H-imidazole / dichloromethane / 5 h / 20 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -15 °C / Inert atmosphere
5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere
6.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 0.5 h / 20 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C / Inert atmosphere
8.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
8.2: 12 h / Inert atmosphere; Reflux
With
pyridine; 1H-imidazole; sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; (R)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol;
5.1: |Dess-Martin Oxidation / 8.1: |Yamaguchi Lactonization;
DOI:10.1016/j.tetasy.2013.07.002
