Technology Process of (1S,2R,4R,5R,9S,10R,13R,14R,15R,19S)-13-Ethyl-4,14-dihydroxy-7,17-bis-(4-methoxy-phenyl)-2,4,10,14,19,20-hexamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.15,9]icosan-11-one
There total 20 articles about (1S,2R,4R,5R,9S,10R,13R,14R,15R,19S)-13-Ethyl-4,14-dihydroxy-7,17-bis-(4-methoxy-phenyl)-2,4,10,14,19,20-hexamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.15,9]icosan-11-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 91 percent / CH2Cl2 / 24 h / Ambient temperature
2: 99 percent / LiAlH4 / diethyl ether / 6 h / Heating
4: 1.) 0.35M iPrMgBr; 2.) LiAlH4 / 1.) THF, 30 min; 2.) THF, reflux, 6 h
5: 72 percent / 80percent NaH/white oil / dimethylformamide / 24 h
6: 1.) N-methylmorpholine N-oxide, 4percent OsO4; 2.) NaIO4 / 1.) tBuOH, acetone, r.t., 10 h; 2.) THF, water, 0 deg C, 3 h
7: 70 percent / petroleum ether / 72 h / 7500600 Torr
8: 82 percent / dichlorodicyanoquinone on molecular sieves / CH2Cl2 / 6 h / -20 °C
9: 1.) N-methylmorpholine N-oxide, 4percent OsO4; 2.) NaIO4 / 1.) tBuOH, acetone, 30 min; 2.) THF, water, 10 min
10: 0.5M Jones reagent / acetone / 0.02 h / -20 °C
11: 2M aq. HCl, 2,4,6-trinitrotoluene / CH2Cl2; methanol; acetone; propan-2-ol / 0.5 h / 35 °C
12: 4-(dimethylamino)pyridine, 2,4,6-trichlorobenzoyl chloride / toluene / 1.) r.t., 1 h; 2.) reflux, 6 h
With
hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; jones reagent; molecular sieve; 2,4,6-Trinitrotoluene; 2,4,6-trichlorobenzoyl chloride; isopropylmagnesium bromide; sodium hydride; 4-methylmorpholine N-oxide; white oil;
In
methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; Petroleum ether;
- Guidance literature:
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Multi-step reaction with 13 steps
1: 1.) O3/O2; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) CH2Cl2, -78 deg C to 0 deg C
2: 91 percent / CH2Cl2 / 24 h / Ambient temperature
3: 99 percent / LiAlH4 / diethyl ether / 6 h / Heating
5: 1.) 0.35M iPrMgBr; 2.) LiAlH4 / 1.) THF, 30 min; 2.) THF, reflux, 6 h
6: 72 percent / 80percent NaH/white oil / dimethylformamide / 24 h
7: 1.) N-methylmorpholine N-oxide, 4percent OsO4; 2.) NaIO4 / 1.) tBuOH, acetone, r.t., 10 h; 2.) THF, water, 0 deg C, 3 h
8: 70 percent / petroleum ether / 72 h / 7500600 Torr
9: 82 percent / dichlorodicyanoquinone on molecular sieves / CH2Cl2 / 6 h / -20 °C
10: 1.) N-methylmorpholine N-oxide, 4percent OsO4; 2.) NaIO4 / 1.) tBuOH, acetone, 30 min; 2.) THF, water, 10 min
11: 0.5M Jones reagent / acetone / 0.02 h / -20 °C
12: 2M aq. HCl, 2,4,6-trinitrotoluene / CH2Cl2; methanol; acetone; propan-2-ol / 0.5 h / 35 °C
13: 4-(dimethylamino)pyridine, 2,4,6-trichlorobenzoyl chloride / toluene / 1.) r.t., 1 h; 2.) reflux, 6 h
With
hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; jones reagent; molecular sieve; 2,4,6-Trinitrotoluene; 2,4,6-trichlorobenzoyl chloride; isopropylmagnesium bromide; oxygen; sodium hydride; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; white oil;
In
methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; Petroleum ether;
- Guidance literature:
-
Multi-step reaction with 10 steps
2: 1.) 0.35M iPrMgBr; 2.) LiAlH4 / 1.) THF, 30 min; 2.) THF, reflux, 6 h
3: 72 percent / 80percent NaH/white oil / dimethylformamide / 24 h
4: 1.) N-methylmorpholine N-oxide, 4percent OsO4; 2.) NaIO4 / 1.) tBuOH, acetone, r.t., 10 h; 2.) THF, water, 0 deg C, 3 h
5: 70 percent / petroleum ether / 72 h / 7500600 Torr
6: 82 percent / dichlorodicyanoquinone on molecular sieves / CH2Cl2 / 6 h / -20 °C
7: 1.) N-methylmorpholine N-oxide, 4percent OsO4; 2.) NaIO4 / 1.) tBuOH, acetone, 30 min; 2.) THF, water, 10 min
8: 0.5M Jones reagent / acetone / 0.02 h / -20 °C
9: 2M aq. HCl, 2,4,6-trinitrotoluene / CH2Cl2; methanol; acetone; propan-2-ol / 0.5 h / 35 °C
10: 4-(dimethylamino)pyridine, 2,4,6-trichlorobenzoyl chloride / toluene / 1.) r.t., 1 h; 2.) reflux, 6 h
With
hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; jones reagent; molecular sieve; 2,4,6-Trinitrotoluene; 2,4,6-trichlorobenzoyl chloride; isopropylmagnesium bromide; sodium hydride; 4-methylmorpholine N-oxide; white oil;
In
methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; Petroleum ether;
