Technology Process of (4S,5R,E)-ethyl 4-(benzyloxy)-5-(tert-butoxycarbonylamino)-5-(4-(tosyloxy)phenyl)pent-2-enoate
There total 12 articles about (4S,5R,E)-ethyl 4-(benzyloxy)-5-(tert-butoxycarbonylamino)-5-(4-(tosyloxy)phenyl)pent-2-enoate 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:
-
diethoxyphosphoryl-acetic acid ethyl ester;
With
sodium hydride;
In
tetrahydrofuran;
at 0 ℃;
Inert atmosphere;
C28H31NO7S;
In
tetrahydrofuran;
at 20 ℃;
for 6h;
diastereoselective reaction;
DOI:10.1016/j.tetlet.2011.07.035
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: sodium azide; ammonium chloride / tetrahydrofuran; water / 12 h / 50 °C
2.1: triphenylphosphine / tetrahydrofuran; water / 3 h / 20 °C
3.1: sodium hydrogencarbonate / tetrahydrofuran; water / 4 h / 20 °C
4.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 0 - 20 °C
5.1: diisobutylaluminium hydride / dichloromethane / 3 h / 0 - 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran; dimethyl sulfoxide / 3 h / 20 °C
7.1: sodium hydride / tetrahydrofuran / 0 °C / Inert atmosphere
7.2: 6 h / 20 °C
With
sodium azide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; ammonium chloride; toluene-4-sulfonic acid; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;
7.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetlet.2011.07.035
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / 0 - 20 °C
2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 3 h / -25 °C / Molecular sieve
3.1: sodium azide; ammonium chloride / tetrahydrofuran; water / 12 h / 50 °C
4.1: triphenylphosphine / tetrahydrofuran; water / 3 h / 20 °C
5.1: sodium hydrogencarbonate / tetrahydrofuran; water / 4 h / 20 °C
6.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 0 - 20 °C
7.1: diisobutylaluminium hydride / dichloromethane / 3 h / 0 - 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran; dimethyl sulfoxide / 3 h / 20 °C
9.1: sodium hydride / tetrahydrofuran / 0 °C / Inert atmosphere
9.2: 6 h / 20 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium azide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; ammonium chloride; toluene-4-sulfonic acid; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;
2.1: Sharpless epoxidation / 9.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetlet.2011.07.035
