Technology Process of (1R,3R,7R,8S,9R,10S,11R)-10-Benzyloxy-7-hydroxy-1-propyl-9-triethylsilanyloxy-11-triisopropylsilanyloxy-2-oxa-tricyclo[5.4.0.03,8]undecan-6-one
There total 16 articles about (1R,3R,7R,8S,9R,10S,11R)-10-Benzyloxy-7-hydroxy-1-propyl-9-triethylsilanyloxy-11-triisopropylsilanyloxy-2-oxa-tricyclo[5.4.0.03,8]undecan-6-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 11 steps
1: 99 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C
2: 81 percent / p-TsOH*H2O / methanol / 0 - 20 °C
3: DMSO; oxalyl chloride; triethylamine / CH2Cl2 / -50 - 20 °C
4: 46 percent / Na2CO3*10H2O / tetrahydrofuran; methanol; H2O / 1 h / 20 °C
5: 97 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C
6: 99 percent / H2 / Pd/C / ethanol / 36 h / 20 °C / 760 Torr
7: DMSO; oxalyl chloride; triethylamine / CH2Cl2 / -78 - 20 °C
8: 154 mg / CH2Cl2 / 0.5 h / 20 °C
9: 79 percent / H2 / Pd/C / ethyl acetate; ethanol / 2 h / 20 °C / 760 Torr
10: n-Bu3SnH; AIBN / benzene / 16 h / Heating
11: 19.5 mg / DMSO; oxalyl chloride; triethylamine / CH2Cl2 / -78 - 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; sodium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; benzene;
3: Swern oxidation / 7: Swern oxidation / 11: Swern oxidation;
DOI:10.1021/ol052321r
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 46 percent / Na2CO3*10H2O / tetrahydrofuran; methanol; H2O / 1 h / 20 °C
2: 97 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C
3: 99 percent / H2 / Pd/C / ethanol / 36 h / 20 °C / 760 Torr
4: DMSO; oxalyl chloride; triethylamine / CH2Cl2 / -78 - 20 °C
5: 154 mg / CH2Cl2 / 0.5 h / 20 °C
6: 79 percent / H2 / Pd/C / ethyl acetate; ethanol / 2 h / 20 °C / 760 Torr
7: n-Bu3SnH; AIBN / benzene / 16 h / Heating
8: 19.5 mg / DMSO; oxalyl chloride; triethylamine / CH2Cl2 / -78 - 20 °C
With
1H-imidazole; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; sodium carbonate; dimethyl sulfoxide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; benzene;
4: Swern oxidation / 8: Swern oxidation;
DOI:10.1021/ol052321r
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 91 percent / imidazole / dimethylformamide / 24 h / 20 °C
2: 99 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C
3: 81 percent / p-TsOH*H2O / methanol / 0 - 20 °C
4: DMSO; oxalyl chloride; triethylamine / CH2Cl2 / -50 - 20 °C
5: 46 percent / Na2CO3*10H2O / tetrahydrofuran; methanol; H2O / 1 h / 20 °C
6: 97 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C
7: 99 percent / H2 / Pd/C / ethanol / 36 h / 20 °C / 760 Torr
8: DMSO; oxalyl chloride; triethylamine / CH2Cl2 / -78 - 20 °C
9: 154 mg / CH2Cl2 / 0.5 h / 20 °C
10: 79 percent / H2 / Pd/C / ethyl acetate; ethanol / 2 h / 20 °C / 760 Torr
11: n-Bu3SnH; AIBN / benzene / 16 h / Heating
12: 19.5 mg / DMSO; oxalyl chloride; triethylamine / CH2Cl2 / -78 - 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; sodium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene;
4: Swern oxidation / 8: Swern oxidation / 12: Swern oxidation;
DOI:10.1021/ol052321r
