Technology Process of (Z)-(2S,8R,9S,12R)-5-(2,2-dimethylhydrazino)-12-<<(4-methoxyphenyl)methoxy>methyl>-8-methyl-9-<(triethylsilyl)oxy>-2-<(4R,6S)-2,2,4-trimethyl-1,3-dioxan-6-yl>-5-tetradecen-7-one
There total 17 articles about (Z)-(2S,8R,9S,12R)-5-(2,2-dimethylhydrazino)-12-<<(4-methoxyphenyl)methoxy>methyl>-8-methyl-9-<(triethylsilyl)oxy>-2-<(4R,6S)-2,2,4-trimethyl-1,3-dioxan-6-yl>-5-tetradecen-7-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1: LiAlH4 / diethyl ether / 4 h / Ambient temperature
2: 1) sodium hydride (60percent in oil) / 1) THF, DMF 0 deg C, 15 min, 2) r.t., 20 h
3: 1) 9-borabicyclo<3.3.1>nonane, 2) NaOH / 1) THF, r.t., 30 min, 2) H2O, r.t., 3 h
4: 1) dimethylsulfoxide, oxalyl chloride, 2) Et3N / 1) CH2Cl2, -78 deg C, 15 min, 2) up to r.t.
6: 1) AlMe3 / 1) toluene, THF, r.t., 30 min, 2) THF, 0 deg C, 2.5 h
7: imidazole / dimethylformamide / 0.5 h / Ambient temperature
With
1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; trimethylaluminum; sodium hydride; dimethyl sulfoxide; triethylamine;
In
diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo00313a011
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 90 percent / Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 16 h / Ambient temperature
2: I2, 0.25 M aq. KHPO4 / tetrahydrofuran / 1) 5 bis 10 deg C, 3 h, 2) r.t, 1 h
3: AIBN, tri-n-butylstannane / benzene / 1 h / Heating
4: p-toluenesulfonic acid / diethyl ether / 17 h / Ambient temperature
5: sodium iodide / acetone / 40 h / Ambient temperature
6: 1) n-BuLi / 1) THF, hexane, - 78 deg C, 30 min, 2) - 35 deg C, 22 h
With
dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; triethylamine; sodium iodide;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetone; benzene;
DOI:10.1021/jo00313a011
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 1) sodium hydride (60percent in oil) / 1) THF, DMF 0 deg C, 15 min, 2) r.t., 20 h
2: 1) 9-borabicyclo<3.3.1>nonane, 2) NaOH / 1) THF, r.t., 30 min, 2) H2O, r.t., 3 h
3: 1) dimethylsulfoxide, oxalyl chloride, 2) Et3N / 1) CH2Cl2, -78 deg C, 15 min, 2) up to r.t.
5: 1) AlMe3 / 1) toluene, THF, r.t., 30 min, 2) THF, 0 deg C, 2.5 h
6: imidazole / dimethylformamide / 0.5 h / Ambient temperature
With
1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; trimethylaluminum; sodium hydride; dimethyl sulfoxide; triethylamine;
In
N,N-dimethyl-formamide;
DOI:10.1021/jo00313a011
