Technology Process of (2S,3S,5R)-2,3-epoxy-5-(t-butyldimethylsilyl)oxy-9-(4-methoxybenzyl)oxy-7-nonyn-1-ol
There total 6 articles about (2S,3S,5R)-2,3-epoxy-5-(t-butyldimethylsilyl)oxy-9-(4-methoxybenzyl)oxy-7-nonyn-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve;
In
dichloromethane;
at -28 ℃;
for 10h;
DOI:10.1016/S0040-4020(01)89344-3
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 1.) 1.56 M n-BuLi, BF3*Et2O; 2.) 60percent NaH in oil / 1.) THF, hexane, -78 deg C, 1 h; 2.) THF, -10 deg C, 1.5 h
2: 93 percent / 1.56 M n-BuLi, BF3*Et2O / tetrahydrofuran / 1 h / -78 °C
3: 92 percent / imidazole / dimethylformamide / 48 h / Ambient temperature
4: 87 percent / 10percent aq. sodium hydroxide / methanol / 3 h / Heating
5: 88 percent / 70percent sodium bismethoxyethoxyaluminum hydride / diethyl ether; toluene / 2 h / Ambient temperature
6: 84 percent / Ti(O-i-Pr)4, 2.4 M t-BuOOH, diisopropyl L-tartarate, 4A molecular sieves / CH2Cl2 / 10 h / -28 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; L-(+)-diisopropyl tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)89344-3
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 93 percent / 1.56 M n-BuLi, BF3*Et2O / tetrahydrofuran / 1 h / -78 °C
2: 92 percent / imidazole / dimethylformamide / 48 h / Ambient temperature
3: 87 percent / 10percent aq. sodium hydroxide / methanol / 3 h / Heating
4: 88 percent / 70percent sodium bismethoxyethoxyaluminum hydride / diethyl ether; toluene / 2 h / Ambient temperature
5: 84 percent / Ti(O-i-Pr)4, 2.4 M t-BuOOH, diisopropyl L-tartarate, 4A molecular sieves / CH2Cl2 / 10 h / -28 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; L-(+)-diisopropyl tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)89344-3
