Technology Process of Selenocarbonic acid O-((1R,3aS,4S,5R,6aR,7S,9aS,10R,10aS)-7-isopropyl-5-methoxymethoxy-1,4,9a-trimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-10-yl) ester Se-phenyl ester
There total 10 articles about Selenocarbonic acid O-((1R,3aS,4S,5R,6aR,7S,9aS,10R,10aS)-7-isopropyl-5-methoxymethoxy-1,4,9a-trimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-10-yl) ester Se-phenyl ester which
guide to synthetic route it.
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synthetic route:
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(Z)-(3S,3aR,5R,6S,6aR,9R,9aS)-3-Isopropyl-6,9-dimethyl-1,2,3,3a,4,5,6,6a,7,8,9,9a-dodecahydro-dicyclopenta[a,d]cycloocten-5-ol
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194794-77-9
Selenocarbonic acid O-((1R,3aS,4S,5R,6aR,7S,9aS,10R,10aS)-7-isopropyl-5-methoxymethoxy-1,4,9a-trimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-10-yl) ester Se-phenyl ester
- Guidance literature:
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Multi-step reaction with 6 steps
1: 95 percent / i-Pr2NEt / CH2Cl2 / 8 h / Ambient temperature
2: 1.) LiBH4, BH3*THF, 2.) 30percent H2O2, 20percent aq. NaOH / 1.) THF, 20 deg C, overnight, 2.) 3 h
3: 83 percent / pyridinium chlorochromate, Al2O3 / CH2Cl2; diethyl ether / 3 h / Ambient temperature
4: 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, -78 deg C to -15 deg C, 1 h, 2.) HMPA, THF, room temp., 4 h
5: 100 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature
6: 1.) DMAP, pyridine, 2.) pyridine / 1.) THF, toluene, room temp., 1 h, 2.) benzene, THF, 4 h
With
pyridine; dmap; aluminum oxide; sodium hydroxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; borane-THF; dihydrogen peroxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate;
In
diethyl ether; dichloromethane;
DOI:10.1021/ja971526v
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(Z)-(3S,3aR,5R,6S,6aR,9R,9aS)-3-Isopropyl-5-methoxymethoxy-6,9-dimethyl-1,2,3,3a,4,5,6,6a,7,8,9,9a-dodecahydro-dicyclopenta[a,d]cyclooctene
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194794-77-9
Selenocarbonic acid O-((1R,3aS,4S,5R,6aR,7S,9aS,10R,10aS)-7-isopropyl-5-methoxymethoxy-1,4,9a-trimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-10-yl) ester Se-phenyl ester
- Guidance literature:
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Multi-step reaction with 5 steps
1: 1.) LiBH4, BH3*THF, 2.) 30percent H2O2, 20percent aq. NaOH / 1.) THF, 20 deg C, overnight, 2.) 3 h
2: 83 percent / pyridinium chlorochromate, Al2O3 / CH2Cl2; diethyl ether / 3 h / Ambient temperature
3: 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, -78 deg C to -15 deg C, 1 h, 2.) HMPA, THF, room temp., 4 h
4: 100 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature
5: 1.) DMAP, pyridine, 2.) pyridine / 1.) THF, toluene, room temp., 1 h, 2.) benzene, THF, 4 h
With
pyridine; dmap; aluminum oxide; sodium hydroxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; borane-THF; dihydrogen peroxide; diisopropylamine; pyridinium chlorochromate;
In
diethyl ether; dichloromethane;
DOI:10.1021/ja971526v
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194794-77-9
Selenocarbonic acid O-((1R,3aS,4S,5R,6aR,7S,9aS,10R,10aS)-7-isopropyl-5-methoxymethoxy-1,4,9a-trimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-10-yl) ester Se-phenyl ester
- Guidance literature:
-
Multi-step reaction with 3 steps
1: 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, -78 deg C to -15 deg C, 1 h, 2.) HMPA, THF, room temp., 4 h
2: 100 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature
3: 1.) DMAP, pyridine, 2.) pyridine / 1.) THF, toluene, room temp., 1 h, 2.) benzene, THF, 4 h
With
pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; diisopropylamine;
In
diethyl ether;
DOI:10.1021/ja971526v