Technology Process of (2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate
There total 4 articles about (2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate 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:
-
(S)-2-benzoyloxypentan-3-one;
With
N,N-dimethyl-ethanamine; dicyclohexylboron chloride;
In
diethyl ether; hexane;
at -78 - 0 ℃;
(E)-5-(4-methoxybenzyloxy)-3-methylpent-2-enal;
In
diethyl ether; hexane;
at -78 - 0 ℃;
With
methanol; dihydrogen peroxide;
In
diethyl ether; hexane; water;
at 0 ℃;
for 2h;
pH=7;
optical yield given as %de;
diastereoselective reaction;
aq. phosphate buffer;
DOI:10.1021/jo901565n
- Guidance literature:
-
(S)-2-benzoyloxypentan-3-one;
With
N,N-dimethyl-ethanamine; dicyclohexylboron chloride;
In
diethyl ether; hexane;
at -78 - 0 ℃;
(E)-5-(4-methoxybenzyloxy)-3-methylpent-2-enal;
In
diethyl ether; hexane;
at -78 - -22 ℃;
for 19h;
Further stages. Title compound not separated from byproducts.;
DOI:10.1021/ja071461o
- Guidance literature:
-
Multi-step reaction with 2 steps
1.1: 98 percent / MnO2 / CH2Cl2 / 2 h / 20 °C
2.1: chlorodicyclohexylborane; Me2NEt / diethyl ether; hexane / -78 - 0 °C
2.2: diethyl ether; hexane / 19 h / -78 - -22 °C
With
manganese(IV) oxide; N,N-dimethyl-ethanamine; dicyclohexylboron chloride;
In
diethyl ether; hexane; dichloromethane;
2.2: Paterson aldol reaction;
DOI:10.1021/ja071461o
