Technology Process of (4R,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-ol
There total 18 articles about (4R,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 98 percent / lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride / tetrahydrofuran / 1 h / -78 °C
2: 96 percent / DBU / CH2Cl2
3: 100 percent / MCPBA / CHCl3 / 48 h / Heating
4: 60 percent / TBAF / tetrahydrofuran / 1 h / 0 °C
5: 57 percent / Ag2O / CH2Cl2
6: 81 percent / K2CO3 / methanol / 8 h / 40 °C
7: 66 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH2Cl2 / 2 h
8: <2.0 equiv. Me2AlCl / CH2Cl2
9: 58 percent / NaBH4 / ethanol; tetrahydrofuran
10: 100 percent / H2 / Pd/C / ethanol
11: 100 percent / H2 / Pt/C / ethanol
12: 87 percent / RuCl2(PPh3)3 / benzene / 6 h
13: 83 percent / DIBAL-H / CH2Cl2 / -78 °C
With
sodium tetrahydroborate; dipyridinium dichromate; tris(triphenylphosphine)ruthenium(II) chloride; Lithium tris[(3-ethyl-3-pentyl)-oxy]aluminohydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dimethylaluminum chloride; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide;
palladium on activated charcoal; platinum on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; benzene;
3: Baeyer-Villiger reaction / 8: Oppenhauer-like oxidation;
DOI:10.1016/S0040-4039(01)01964-5
- Guidance literature:
-
Multi-step reaction with 15 steps
1.1: O3 / CH2Cl2; methanol / 1 h / -60 °C
1.2: p-TsOH / methanol / 1 h / -60 - 0 °C
2.1: 100 percent / HClO4 / H2O; tetrahydrofuran
3.1: 98 percent / lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride / tetrahydrofuran / 1 h / -78 °C
4.1: 96 percent / DBU / CH2Cl2
5.1: 100 percent / MCPBA / CHCl3 / 48 h / Heating
6.1: 60 percent / TBAF / tetrahydrofuran / 1 h / 0 °C
7.1: 57 percent / Ag2O / CH2Cl2
8.1: 81 percent / K2CO3 / methanol / 8 h / 40 °C
9.1: 66 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH2Cl2 / 2 h
10.1: <2.0 equiv. Me2AlCl / CH2Cl2
11.1: 58 percent / NaBH4 / ethanol; tetrahydrofuran
12.1: 100 percent / H2 / Pd/C / ethanol
13.1: 100 percent / H2 / Pt/C / ethanol
14.1: 87 percent / RuCl2(PPh3)3 / benzene / 6 h
15.1: 83 percent / DIBAL-H / CH2Cl2 / -78 °C
With
sodium tetrahydroborate; dipyridinium dichromate; tris(triphenylphosphine)ruthenium(II) chloride; perchloric acid; Lithium tris[(3-ethyl-3-pentyl)-oxy]aluminohydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dimethylaluminum chloride; diisobutylaluminium hydride; potassium carbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide;
palladium on activated charcoal; platinum on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; benzene;
5.1: Baeyer-Villiger reaction / 10.1: Oppenhauer-like oxidation;
DOI:10.1016/S0040-4039(01)01964-5
![(4R,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-one](/Databaselist/images/loading.webp)
