Technology Process of (1R,2R,3R,4R,5R,6S,8R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-11-methylene-12-oxa-tricyclo[6.3.1.01,6]dodecane
There total 14 articles about (1R,2R,3R,4R,5R,6S,8R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-11-methylene-12-oxa-tricyclo[6.3.1.01,6]dodecane 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 10 steps
1.1: chlorodicyclohexylborane; triethylamine / diethyl ether; hexane / 2 h / -78 °C
1.2: diethyl ether; hexane / 40 h / -15 °C
2.1: 11.0 g / LiBH4 / diethyl ether; hexane; tetrahydrofuran / 3 h / -78 °C
3.1: tetrahydrofuran / 0.58 h / -78 - 20 °C
4.1: 2,6-lutidine / CH2Cl2 / -78 - 0 °C
5.1: 2.6 g / citric acid / methanol / 3 h / 20 °C
6.1: VO(acac)2; tert-butylhydroperoxide / CH2Cl2 / 1.08 h / 20 °C
7.1: 10.6 g / pyridine; DMAP / 0 - 20 °C
8.1: DBU / CH2Cl2 / 18 h / 20 °C
9.1: H2 / Pd(OH)2/C / ethyl acetate / 2.17 h / 760 Torr
10.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C
10.2: 5.7 g / tetrahydrofuran / 1.5 h / 80 °C
With
pyridine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; lithium borohydride; bis(acetylacetonate)oxovanadium; dicyclohexylboron chloride; potassium tert-butylate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; citric acid;
palladium dihydroxide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate;
DOI:10.1021/ol062234e
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 97 percent / molecular sieves 4 Angstroem; 4-methylmorpholine N-oxide; TPAP / CH2Cl2; acetonitrile / 0 - 20 °C
2.1: chlorodicyclohexylborane; triethylamine / diethyl ether; hexane / 2 h / -78 °C
2.2: diethyl ether; hexane / 40 h / -15 °C
3.1: 11.0 g / LiBH4 / diethyl ether; hexane; tetrahydrofuran / 3 h / -78 °C
4.1: tetrahydrofuran / 0.58 h / -78 - 20 °C
5.1: 2,6-lutidine / CH2Cl2 / -78 - 0 °C
6.1: 2.6 g / citric acid / methanol / 3 h / 20 °C
7.1: VO(acac)2; tert-butylhydroperoxide / CH2Cl2 / 1.08 h / 20 °C
8.1: 10.6 g / pyridine; DMAP / 0 - 20 °C
9.1: DBU / CH2Cl2 / 18 h / 20 °C
10.1: H2 / Pd(OH)2/C / ethyl acetate / 2.17 h / 760 Torr
11.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C
11.2: 5.7 g / tetrahydrofuran / 1.5 h / 80 °C
With
pyridine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; lithium borohydride; tetrapropylammonium perruthennate; bis(acetylacetonate)oxovanadium; 4 A molecular sieve; dicyclohexylboron chloride; potassium tert-butylate; hydrogen; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; citric acid;
palladium dihydroxide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/ol062234e
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: tetrahydrofuran / 0.58 h / -78 - 20 °C
2.1: 2,6-lutidine / CH2Cl2 / -78 - 0 °C
3.1: 2.6 g / citric acid / methanol / 3 h / 20 °C
4.1: VO(acac)2; tert-butylhydroperoxide / CH2Cl2 / 1.08 h / 20 °C
5.1: 10.6 g / pyridine; DMAP / 0 - 20 °C
6.1: DBU / CH2Cl2 / 18 h / 20 °C
7.1: H2 / Pd(OH)2/C / ethyl acetate / 2.17 h / 760 Torr
8.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C
8.2: 5.7 g / tetrahydrofuran / 1.5 h / 80 °C
With
pyridine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; bis(acetylacetonate)oxovanadium; potassium tert-butylate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; citric acid;
palladium dihydroxide;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1021/ol062234e
