Technology Process of (Z)-(9S,10R)-9-(tert-Butyl-diphenyl-silanyloxy)-10-((1E,3Z)-4-iodo-buta-1,3-dienyl)-3,4,5,8,9,10-hexahydro-oxecin-2-one
There total 9 articles about (Z)-(9S,10R)-9-(tert-Butyl-diphenyl-silanyloxy)-10-((1E,3Z)-4-iodo-buta-1,3-dienyl)-3,4,5,8,9,10-hexahydro-oxecin-2-one which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1: HCl / diethyl ether / 0.25 h
2: pyridine / 0.5 h / Ambient temperature
3: 98 percent / BCl3*Me2S / diethyl ether / 0.17 h / Ambient temperature
4: 1.) NaN(TMS)2 / 1.) toluene, THF, from 0 deg C to -70 deg C, 2.) toluene, THF, from -70 deg C to 0 deg C
5: 96 percent
6: 85 percent / HF, pyridine / tetrahydrofuran
7: DMSO, (COCl)2 / -78 °C
8: 77 percent / CH2Cl2 / 16 h / Ambient temperature
9: 1.) NaHMDS, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) / 1.) RT, 1 min, 2.) from -90 deg C to RT, 5 min
With
pyridine; hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; oxalyl dichloride; boron trichloride - methyl sulfide complex; hydrogen fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja00066a056
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 1.) NaN(TMS)2 / 1.) toluene, THF, from 0 deg C to -70 deg C, 2.) toluene, THF, from -70 deg C to 0 deg C
2: 96 percent
3: 85 percent / HF, pyridine / tetrahydrofuran
4: DMSO, (COCl)2 / -78 °C
5: 77 percent / CH2Cl2 / 16 h / Ambient temperature
6: 1.) NaHMDS, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) / 1.) RT, 1 min, 2.) from -90 deg C to RT, 5 min
With
pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; oxalyl dichloride; hydrogen fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide;
In
tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00066a056
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 98 percent / BCl3*Me2S / diethyl ether / 0.17 h / Ambient temperature
2: 1.) NaN(TMS)2 / 1.) toluene, THF, from 0 deg C to -70 deg C, 2.) toluene, THF, from -70 deg C to 0 deg C
3: 96 percent
4: 85 percent / HF, pyridine / tetrahydrofuran
5: DMSO, (COCl)2 / -78 °C
6: 77 percent / CH2Cl2 / 16 h / Ambient temperature
7: 1.) NaHMDS, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) / 1.) RT, 1 min, 2.) from -90 deg C to RT, 5 min
With
pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; oxalyl dichloride; boron trichloride - methyl sulfide complex; hydrogen fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja00066a056