Technology Process of (2R,3S)-3-((3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-hydroxydeca-1,9-dien-3-yloxy)-2-hydroxytridecyl 4-methylbenzenesulfonate
There total 17 articles about (2R,3S)-3-((3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-hydroxydeca-1,9-dien-3-yloxy)-2-hydroxytridecyl 4-methylbenzenesulfonate 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:
-
(3S,4S,7S,8S)-4,7-bis(benzyloxy)deca-1,9-diene-3,8-diol; ((2R,3R)-3-decyloxiran-2-yl)methyl 4-methylbenzenesulfonate;
With
boron trifluoride diethyl etherate;
In
dichloromethane;
at 0 - 20 ℃;
for 39h;
Inert atmosphere;
Molecular sieve;
With
water;
In
dichloromethane;
for 0.166667h;
regioselective reaction;
Cooling with ice;
DOI:10.1016/j.tet.2011.07.079
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: water / toluene / 0.08 h / 20 °C
1.2: 2 h / 20 °C
2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
3.1: camphor-10-sulfonic acid / dichloromethane / 4 h / Inert atmosphere
4.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 96 h / Inert atmosphere; Reflux
5.1: platinum oxide on carbon; hydrogen / methanol; benzene / 24 h / 20 °C / 7500.75 Torr / Inert atmosphere
6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
7.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 - 20 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.58 h / 0 - 20 °C / Inert atmosphere
9.1: ethanol; magnesium; mercury dichloride / 4 h / 0 - 20 °C / Inert atmosphere
10.1: boron trifluoride diethyl etherate / dichloromethane / 39 h / 0 - 20 °C / Inert atmosphere; Molecular sieve
10.2: 0.17 h / Cooling with ice
With
Hoveyda-Grubbs catalyst second generation; ethanol; trifluorormethanesulfonic acid; platinum oxide on carbon; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; mercury dichloride;
In
tetrahydrofuran; methanol; dichloromethane; cyclohexane; toluene; benzene;
DOI:10.1016/j.tet.2011.07.079
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere
2.1: water / toluene / 0.08 h / 20 °C
2.2: 2 h / 20 °C
3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
4.1: camphor-10-sulfonic acid / dichloromethane / 4 h / Inert atmosphere
5.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 96 h / Inert atmosphere; Reflux
6.1: platinum oxide on carbon; hydrogen / methanol; benzene / 24 h / 20 °C / 7500.75 Torr / Inert atmosphere
7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
8.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 - 20 °C / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.58 h / 0 - 20 °C / Inert atmosphere
10.1: ethanol; magnesium; mercury dichloride / 4 h / 0 - 20 °C / Inert atmosphere
11.1: boron trifluoride diethyl etherate / dichloromethane / 39 h / 0 - 20 °C / Inert atmosphere; Molecular sieve
11.2: 0.17 h / Cooling with ice
With
1H-imidazole; Hoveyda-Grubbs catalyst second generation; ethanol; trifluorormethanesulfonic acid; platinum oxide on carbon; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; mercury dichloride;
In
tetrahydrofuran; methanol; dichloromethane; cyclohexane; toluene; benzene;
DOI:10.1016/j.tet.2011.07.079
