Technology Process of (5S,6S)-8-(tert-butyldimethylsilyloxy)-6-methoxy-5-(4-methoxybenzyloxy)-3-methyleneoctan-2-one
There total 6 articles about (5S,6S)-8-(tert-butyldimethylsilyloxy)-6-methoxy-5-(4-methoxybenzyloxy)-3-methyleneoctan-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:
-
Multi-step reaction with 6 steps
1.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
1.2: 16 h / 0 - 20 °C / Inert atmosphere
2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 9 h / 20 °C / Inert atmosphere
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -60 °C
3.2: -60 - 20 °C
4.1: titanium(IV) trichloride isopropoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere
4.2: -78 °C / Inert atmosphere
5.1: trifluorormethanesulfonic acid / diethyl ether / 1.75 h / -20 - 20 °C
6.1: tert.-butyl lithium / diethyl ether; pentane / 0.58 h / -78 °C / Inert atmosphere
6.2: 1.5 h / -78 °C / Inert atmosphere
With
oxalyl dichloride; titanium(IV) trichloride isopropoxide; trifluorormethanesulfonic acid; palladium 10% on activated carbon; hydrogen; tert.-butyl lithium; sodium hydride; dimethyl sulfoxide;
In
tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; pentane;
3.1: |Swern Oxidation / 3.2: |Swern Oxidation;
DOI:10.1021/ol400046n
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 9 h / 20 °C / Inert atmosphere
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -60 °C
2.2: -60 - 20 °C
3.1: titanium(IV) trichloride isopropoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere
3.2: -78 °C / Inert atmosphere
4.1: trifluorormethanesulfonic acid / diethyl ether / 1.75 h / -20 - 20 °C
5.1: tert.-butyl lithium / diethyl ether; pentane / 0.58 h / -78 °C / Inert atmosphere
5.2: 1.5 h / -78 °C / Inert atmosphere
With
oxalyl dichloride; titanium(IV) trichloride isopropoxide; trifluorormethanesulfonic acid; palladium 10% on activated carbon; hydrogen; tert.-butyl lithium; dimethyl sulfoxide;
In
diethyl ether; dichloromethane; ethyl acetate; pentane;
2.1: |Swern Oxidation / 2.2: |Swern Oxidation;
DOI:10.1021/ol400046n
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: pyridinium p-toluenesulfonate / acetonitrile / 4 h / 0 - 96 °C
2.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
2.2: 16 h / 0 - 20 °C / Inert atmosphere
3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 9 h / 20 °C / Inert atmosphere
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -60 °C
4.2: -60 - 20 °C
5.1: titanium(IV) trichloride isopropoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere
5.2: -78 °C / Inert atmosphere
6.1: trifluorormethanesulfonic acid / diethyl ether / 1.75 h / -20 - 20 °C
7.1: tert.-butyl lithium / diethyl ether; pentane / 0.58 h / -78 °C / Inert atmosphere
7.2: 1.5 h / -78 °C / Inert atmosphere
With
oxalyl dichloride; titanium(IV) trichloride isopropoxide; trifluorormethanesulfonic acid; palladium 10% on activated carbon; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide;
In
tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetonitrile; pentane;
4.1: |Swern Oxidation / 4.2: |Swern Oxidation;
DOI:10.1021/ol400046n
