Technology Process of (2S,3S)-cis-5,7-bis(benzyloxy)-8-benzyl-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate
There total 9 articles about (2S,3S)-cis-5,7-bis(benzyloxy)-8-benzyl-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate which
guide to synthetic route it.
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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)-8-benzyl-2-[3,4-bis(benzyloxy)phenyl]chroman-3-ol;
With
dmap;
In
dichloromethane;
at 0 ℃;
DOI:10.1016/j.bmc.2004.12.056
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 46 percent / H2SO4; SiO2 / CH2Cl2 / 20 °C
2.1: imidazole / 72 h / 20 °C
3.1: AD-mix-β; methanesulfonamide / 0 °C
4.1: 2.4 g / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C
5.1: triethyl orthoformate; PPTS / 1,2-dichloro-ethane / 5 h / 55 °C
5.2: 77 percent / K2CO3 / 1,2-dimethoxy-ethane; methanol / 20 °C
6.1: 86 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
7.1: 90 percent / L-Selectride / tetrahydrofuran / 8 h / -78 °C
8.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating
8.2: 91 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 0 °C
With
1H-imidazole; oxalyl dichloride; methanesulfonamide; AD-mix-β; sulfuric acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; silica gel; L-Selectride; Dess-Martin periodane; orthoformic acid triethyl ester;
In
tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
1.1: Friedel-Crafts reaction;
DOI:10.1016/j.bmc.2004.12.056
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: imidazole / 72 h / 20 °C
2.1: AD-mix-β; methanesulfonamide / 0 °C
3.1: 2.4 g / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C
4.1: triethyl orthoformate; PPTS / 1,2-dichloro-ethane / 5 h / 55 °C
4.2: 77 percent / K2CO3 / 1,2-dimethoxy-ethane; methanol / 20 °C
5.1: 86 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
6.1: 90 percent / L-Selectride / tetrahydrofuran / 8 h / -78 °C
7.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating
7.2: 91 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 0 °C
With
1H-imidazole; oxalyl dichloride; methanesulfonamide; AD-mix-β; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; L-Selectride; Dess-Martin periodane; orthoformic acid triethyl ester;
In
tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2004.12.056
![(2S,3S)-cis-5,7-bis(benzyloxy)-8-benzyl-2-[3,4-bis(benzyloxy)phenyl]chroman-3-ol](/Databaselist/images/loading.webp)
