Technology Process of (2S,3S)-5,7-bis(benzyloxy)-2-(3-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate
There total 9 articles about (2S,3S)-5,7-bis(benzyloxy)-2-(3-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)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:
-
3,4,5-tris(benzyloxy)benzoyl chloride;
With
oxalyl dichloride;
In
dichloromethane; N,N-dimethyl-formamide;
for 3h;
Heating;
(2S,3S)-cis-5,7-bis(benzyloxy)-2-(3-benzyloxyphenyl)chroman-3-ol;
With
dmap;
In
dichloromethane;
at 0 ℃;
DOI:10.1016/j.bmc.2004.12.056
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 64 percent / butanethiol; sodium hydride / dimethylformamide / 1.5 h / 150 °C
2.1: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 °C
3.1: imidazole / 72 h / 20 °C
4.1: AD-mix-α; methanesulfonamide / 0 °C
5.1: tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C
6.1: PPTS / 1,2-dichloro-ethane / 0.33 h / 20 °C
7.1: acetyl bromide / CH2Cl2 / 0.75 h / -5 - 0 °C
8.1: K2CO3 / acetone; methanol / 20 °C
9.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating
9.2: 80 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 0 °C
With
1H-imidazole; AD-mix-α; oxalyl dichloride; Acetyl bromide; n-butanethiol; methanesulfonamide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;
2.1: Mitsunobu reaction;
DOI:10.1016/j.bmc.2004.12.056
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 °C
2.1: imidazole / 72 h / 20 °C
3.1: AD-mix-α; methanesulfonamide / 0 °C
4.1: tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C
5.1: PPTS / 1,2-dichloro-ethane / 0.33 h / 20 °C
6.1: acetyl bromide / CH2Cl2 / 0.75 h / -5 - 0 °C
7.1: K2CO3 / acetone; methanol / 20 °C
8.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating
8.2: 80 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 0 °C
With
1H-imidazole; AD-mix-α; oxalyl dichloride; Acetyl bromide; methanesulfonamide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium carbonate; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;
1.1: Mitsunobu reaction;
DOI:10.1016/j.bmc.2004.12.056
