Technology Process of (5R,7R,8R,9S,10S,13R,14S,17R)-17-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,5-dimethyl-hexyl]-7-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one O-benzyl-oxime
There total 10 articles about (5R,7R,8R,9S,10S,13R,14S,17R)-17-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,5-dimethyl-hexyl]-7-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one O-benzyl-oxime which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 10 steps
1: (COCl)2 / CH2Cl2 / 2 h / Heating
2: 60 percent / cadmium bromide / benzene / 1 h / Ambient temperature
3: 80 percent / sodium borohydride, calcium chloride / tetrahydrofuran / 5 h / Ambient temperature
4: 90 percent / imidazole / CH2Cl2 / 16 h / Ambient temperature
5: 46 percent / chromium hexacarbonyl, tert-butyl hydroperoxide / acetonitrile / 12 h / Heating
6: 81 percent / Li, liq. NH3 / diethyl ether / 0.17 h / -78 °C
7: 80 percent / K-selectride / tetrahydrofuran / 5 h / -50 °C
8: 88 percent / NaCN / methanol / 8 h / Heating
9: 59 percent / aluminum tri-tert-butoxide, cyclohexanone / toluene / 20 h / 120 °C
10: 97 percent / C5H5N / ethanol / 16 h / Heating
With
pyridine; 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; oxalyl dichloride; sodium cyanide; ammonia; cyclohexanone; lithium; aluminum tri-tert-butoxide; potassium tri-sec-butyl-borohydride; chromium(0) hexacarbonyl; calcium chloride; cadmium(II) bromide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; acetonitrile; benzene;
DOI:10.1016/0040-4039(94)88254-1
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 80 percent / sodium borohydride, calcium chloride / tetrahydrofuran / 5 h / Ambient temperature
2: 90 percent / imidazole / CH2Cl2 / 16 h / Ambient temperature
3: 46 percent / chromium hexacarbonyl, tert-butyl hydroperoxide / acetonitrile / 12 h / Heating
4: 81 percent / Li, liq. NH3 / diethyl ether / 0.17 h / -78 °C
5: 80 percent / K-selectride / tetrahydrofuran / 5 h / -50 °C
6: 88 percent / NaCN / methanol / 8 h / Heating
7: 59 percent / aluminum tri-tert-butoxide, cyclohexanone / toluene / 20 h / 120 °C
8: 97 percent / C5H5N / ethanol / 16 h / Heating
With
pyridine; 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium cyanide; ammonia; cyclohexanone; lithium; aluminum tri-tert-butoxide; potassium tri-sec-butyl-borohydride; chromium(0) hexacarbonyl; calcium chloride;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; acetonitrile;
DOI:10.1016/0040-4039(94)88254-1