Technology Process of (E)-(3R,5R,6S,7S,9R,13S,14R)-14-ethyl-13-hydroxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione
There total 9 articles about (E)-(3R,5R,6S,7S,9R,13S,14R)-14-ethyl-13-hydroxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione 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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1353285-77-4
(E)-(3R,4S,5S,6S,7S,9R,13S,14R)-14-ethyl-4,13-dihydroxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,10-dione
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1353285-79-6
(E)-(3R,5R,6S,7S,9R,13S,14R)-14-ethyl-13-hydroxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione
- Guidance literature:
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With
Dess-Martin periodane;
In
dichloromethane;
at 20 ℃;
for 0.5h;
DOI:10.1021/jo201158q
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1353285-79-6
(E)-(3R,5R,6S,7S,9R,13S,14R)-14-ethyl-13-hydroxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 3 h / 20 °C
1.2: 15 h / 20 °C
2.1: 10-camphorsufonic acid / methanol / 1 h / 0 °C
3.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
4.1: tetrahydrofuran / 0.33 h / 20 °C
4.2: 20 °C
5.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 18 h / 20 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C
8.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,4,6-trichlorobenzoyl chloride; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane;
1.1: Yamaguchi esterification / 1.2: Yamaguchi esterification / 4.1: Grignard reaction;
DOI:10.1021/jo201158q
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1353285-79-6
(E)-(3R,5R,6S,7S,9R,13S,14R)-14-ethyl-13-hydroxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 3 h / 20 °C
1.2: 15 h / 20 °C
2.1: 10-camphorsufonic acid / methanol / 1 h / 0 °C
3.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
4.1: tetrahydrofuran / 0.33 h / 20 °C
4.2: 20 °C
5.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 18 h / 20 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C
8.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,4,6-trichlorobenzoyl chloride; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane;
1.1: Yamaguchi esterification / 1.2: Yamaguchi esterification / 4.1: Grignard reaction;
DOI:10.1021/jo201158q
