Technology Process of (2R,4aR,6R,7S,8R,8aR)-6-[(R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
There total 13 articles about (2R,4aR,6R,7S,8R,8aR)-6-[(R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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 12 steps
1.1: potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran / -78 °C
1.2: diisobutyl aluminium hydride / CH2Cl2 / -78 °C
2.1: imidazole / dimethylformamide / 20 °C
3.1: 97 percent / di-tert-butyldiphenyllithium / tetrahydrofuran / -78 °C
4.1: 82 percent / (-)-diethyl tartrate; 4 Angstroem molecular sieves; tBuOOH / Ti(iPrO)4 / CH2Cl2 / -20 °C
5.1: 80 percent / Ti(iPrO)4 / tetrahydrofuran / 20 °C
6.1: 99 percent / Et3N / CH2Cl2 / 20 °C
7.1: 99 percent / dimethyl dioxirane / CH2Cl2 / -20 °C
8.1: camphorsulfonic acid / CH2Cl2; methanol / -20 °C
9.1: 83 percent / camphorsulfonic acid / CH2Cl2 / 20 °C
10.1: 76 percent / diisobutyl aluminium hydride / CH2Cl2 / -78 °C
11.1: 80 percent / camphorsulfonic acid / CH2Cl2 / 20 °C
12.1: 98 percent / KH / tetrahydrofuran / 0 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; 4 A molecular sieve; camphor-10-sulfonic acid; 3,3-dimethyldioxirane; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium 4,4′-di-tert-butylbiphenylide; (-)-diethyl tartrate; triethylamine;
titanium(IV) isopropylate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
1.1: Alkylation / 1.2: Reduction / 2.1: silylation / 3.1: Hydrolysis / 4.1: Epoxidation / 5.1: benzoylation / 6.1: silylation / 7.1: Epoxidation / 8.1: Hydrolysis / 9.1: Cyclization / 10.1: Hydrogenolysis / 11.1: Condensation / 12.1: benzylation;
DOI:10.1016/S0040-4039(99)01481-1
- Guidance literature:
-
Multi-step reaction with 11 steps
1: imidazole / dimethylformamide / 20 °C
2: 97 percent / di-tert-butyldiphenyllithium / tetrahydrofuran / -78 °C
3: 82 percent / (-)-diethyl tartrate; 4 Angstroem molecular sieves; tBuOOH / Ti(iPrO)4 / CH2Cl2 / -20 °C
4: 80 percent / Ti(iPrO)4 / tetrahydrofuran / 20 °C
5: 99 percent / Et3N / CH2Cl2 / 20 °C
6: 99 percent / dimethyl dioxirane / CH2Cl2 / -20 °C
7: camphorsulfonic acid / CH2Cl2; methanol / -20 °C
8: 83 percent / camphorsulfonic acid / CH2Cl2 / 20 °C
9: 76 percent / diisobutyl aluminium hydride / CH2Cl2 / -78 °C
10: 80 percent / camphorsulfonic acid / CH2Cl2 / 20 °C
11: 98 percent / KH / tetrahydrofuran / 0 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve; camphor-10-sulfonic acid; 3,3-dimethyldioxirane; potassium hydride; diisobutylaluminium hydride; lithium 4,4′-di-tert-butylbiphenylide; (-)-diethyl tartrate; triethylamine;
titanium(IV) isopropylate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
1: silylation / 2: Hydrolysis / 3: Epoxidation / 4: benzoylation / 5: silylation / 6: Epoxidation / 7: Hydrolysis / 8: Cyclization / 9: Hydrogenolysis / 10: Condensation / 11: benzylation;
DOI:10.1016/S0040-4039(99)01481-1
