Technology Process of Trifluoro-acetic acid (1R,2R,3S)-3-methoxy-2-methyl-5-(toluene-4-sulfonyloxy)-1-((R)-1-{(4R,5R,6S)-2,2,5-trimethyl-6-[(S)-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl]-[1,3]dioxan-4-yl}-ethyl)-pentyl ester
There total 12 articles about Trifluoro-acetic acid (1R,2R,3S)-3-methoxy-2-methyl-5-(toluene-4-sulfonyloxy)-1-((R)-1-{(4R,5R,6S)-2,2,5-trimethyl-6-[(S)-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl]-[1,3]dioxan-4-yl}-ethyl)-pentyl ester 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: 2,6-lutidine / CH2Cl2 / 0 °C
2: lithium 1,1,3,3-tetramethyl-1,3-diphenyldisilazide, bis(cyclopentadienyl)zirconium dichloride / tetrahydrofuran / -40 deg C -> -20 deg C
3: diisobutylaluminium hydride / diethyl ether / -78 °C
4: conc. H2SO4 / acetone / 0 °C
5: n-Bu4NF / tetrahydrofuran / 36 h / 40 °C
6: imidazole / tetrahydrofuran
7: Collins-Ratcliffe oxidation
8: tetrahydrofuran / -78 °C
9: 1.) NaBH4, 2.) hydrogen / 2.) 5percent Pd/C
10: triethylamine / benzene
11: hydrolysis
12: C5H5N / CH2Cl2 / 48 h / 0 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; zirconocene dichloride; lithium bis(dimethylphenylsilyl)amide; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetone; benzene;
DOI:10.1021/ja00384a063
- Guidance literature:
-
Multi-step reaction with 11 steps
1: lithium 1,1,3,3-tetramethyl-1,3-diphenyldisilazide, bis(cyclopentadienyl)zirconium dichloride / tetrahydrofuran / -40 deg C -> -20 deg C
2: diisobutylaluminium hydride / diethyl ether / -78 °C
3: conc. H2SO4 / acetone / 0 °C
4: n-Bu4NF / tetrahydrofuran / 36 h / 40 °C
5: imidazole / tetrahydrofuran
6: Collins-Ratcliffe oxidation
7: tetrahydrofuran / -78 °C
8: 1.) NaBH4, 2.) hydrogen / 2.) 5percent Pd/C
9: triethylamine / benzene
10: hydrolysis
11: C5H5N / CH2Cl2 / 48 h / 0 °C
With
pyridine; 1H-imidazole; sodium tetrahydroborate; zirconocene dichloride; lithium bis(dimethylphenylsilyl)amide; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetone; benzene;
DOI:10.1021/ja00384a063
- Guidance literature:
-
Multi-step reaction with 7 steps
1: imidazole / tetrahydrofuran
2: Collins-Ratcliffe oxidation
3: tetrahydrofuran / -78 °C
4: 1.) NaBH4, 2.) hydrogen / 2.) 5percent Pd/C
5: triethylamine / benzene
6: hydrolysis
7: C5H5N / CH2Cl2 / 48 h / 0 °C
With
pyridine; 1H-imidazole; sodium tetrahydroborate; hydrogen; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/ja00384a063