Technology Process of (1S,12S)-14-[(E)-18-(tert-butyldiphenylsilanyloxy)vinyl]-3-methyl-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.02,10.04,9]hexadeca-2(10),4,6,8,13-pentane
There total 8 articles about (1S,12S)-14-[(E)-18-(tert-butyldiphenylsilanyloxy)vinyl]-3-methyl-16-(toluene-4-sulfonyl)-3,16-diazatetracyclo[10.3.1.02,10.04,9]hexadeca-2(10),4,6,8,13-pentane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 72 percent / lithium naphthalenide; DMPU / tetrahydrofuran / -78 - 20 °C
2.1: 61 percent / KMnO4; nBu4NBr / CH2Cl2 / 3 - 20 °C
3.1: Pb(OAc)4; NaHCO3 / 1,2-dichloro-ethane / 0.5 h / 0 °C
3.2: 94 percent / MgSO4; TEA / CH2Cl2 / 0.83 h / 20 °C
4.1: 95 percent / DMAP; DBU / CH2Cl2 / 1.5 h / 0 °C
With
lead(IV) acetate; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium permanganate; tetrabutylammomium bromide; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; naphthalen-1-yl-lithium;
In
tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;
3.2: Pictet-Spengler-type bicyclization;
DOI:10.1016/j.tetlet.2005.04.033
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 80 percent / KOH; tosyl chloride / diethyl ether; tetrahydrofuran
2.1: 72 percent / lithium naphthalenide; DMPU / tetrahydrofuran / -78 - 20 °C
3.1: 61 percent / KMnO4; nBu4NBr / CH2Cl2 / 3 - 20 °C
4.1: Pb(OAc)4; NaHCO3 / 1,2-dichloro-ethane / 0.5 h / 0 °C
4.2: 94 percent / MgSO4; TEA / CH2Cl2 / 0.83 h / 20 °C
5.1: 95 percent / DMAP; DBU / CH2Cl2 / 1.5 h / 0 °C
With
lead(IV) acetate; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; potassium permanganate; tetrabutylammomium bromide; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; naphthalen-1-yl-lithium; p-toluenesulfonyl chloride;
In
tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane;
4.2: Pictet-Spengler-type bicyclization;
DOI:10.1016/j.tetlet.2005.04.033