Technology Process of (2R,4S,7R,8R,9R,11R)-1-Azido-9-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-2,4,11-trimethyl-14-triethylsilanyl-7-triethylsilanyloxy-tetradec-13-yn-5-one
There total 13 articles about (2R,4S,7R,8R,9R,11R)-1-Azido-9-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-2,4,11-trimethyl-14-triethylsilanyl-7-triethylsilanyloxy-tetradec-13-yn-5-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 9 steps
1.1: 93 percent / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 1.5 h
2.1: 58 percent / H2 / Pd-BaSO4 / ethyl acetate / 6 h / 760 Torr
3.1: 87 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h
4.1: dicyclohexylchloroborane; triethylamine / diethyl ether / 2 h / 0 °C
4.2: 69 percent / H2O2; phosphate buffer / diethyl ether; methanol; H2O / -78 - 20 °C / pH 7
5.1: 83 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
6.1: 92 percent / NaBH4 / methanol / 1 h / 0 °C
7.1: K2CO3 / methanol / 5 h
7.2: 70 percent / NaIO4; acetic acid / methanol / 4 h / pH 9
8.1: 66 percent / MgBr2*OEt2 / CH2Cl2 / -78 - -25 °C
9.1: 92 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -10 °C
With
2,6-dimethylpyridine; dmap; sodium tetrahydroborate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; dicyclohexylboron chloride; hydrogen; potassium carbonate; triethylamine; magnesium bromide;
palladium on barium sulfate;
In
methanol; diethyl ether; dichloromethane; ethyl acetate;
8.1: Mukaiyama aldol reaction;
DOI:10.1016/j.tet.2006.01.112
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 58 percent / H2 / Pd-BaSO4 / ethyl acetate / 6 h / 760 Torr
2.1: 87 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h
3.1: dicyclohexylchloroborane; triethylamine / diethyl ether / 2 h / 0 °C
3.2: 69 percent / H2O2; phosphate buffer / diethyl ether; methanol; H2O / -78 - 20 °C / pH 7
4.1: 83 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
5.1: 92 percent / NaBH4 / methanol / 1 h / 0 °C
6.1: K2CO3 / methanol / 5 h
6.2: 70 percent / NaIO4; acetic acid / methanol / 4 h / pH 9
7.1: 66 percent / MgBr2*OEt2 / CH2Cl2 / -78 - -25 °C
8.1: 92 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -10 °C
With
2,6-dimethylpyridine; sodium tetrahydroborate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; dicyclohexylboron chloride; hydrogen; potassium carbonate; triethylamine; magnesium bromide;
palladium on barium sulfate;
In
methanol; diethyl ether; dichloromethane; ethyl acetate;
7.1: Mukaiyama aldol reaction;
DOI:10.1016/j.tet.2006.01.112
