Technology Process of (S)-2-{(5S,6S)-6-[(1E,5E)-(3S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,3,5-trimethyl-hepta-1,5-dienyl]-5-methyl-5,6-dihydro-4H-pyran-2-yl}-2-(4-methoxy-benzyloxy)-butyric acid methyl ester
There total 10 articles about (S)-2-{(5S,6S)-6-[(1E,5E)-(3S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,3,5-trimethyl-hepta-1,5-dienyl]-5-methyl-5,6-dihydro-4H-pyran-2-yl}-2-(4-methoxy-benzyloxy)-butyric acid methyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 98 percent / PPTS / dimethylformamide / 2 h / 55 °C / 25 Torr
2: i-Bu2AlH / CH2Cl2 / 2 h / -78 °C
3: pyridinium dichromate / dimethylformamide / 96 h / Ambient temperature
4: diethyl ether; CHCl3
5: 74 percent / n-Bu4NF / tetrahydrofuran / 48 h / Ambient temperature
6: 82 percent / 1.) Me2SO, (COCl)2; 2.) Et3N / CH2Cl2 / -78 °C
7: 82 percent / n-BuLi / tetrahydrofuran / -78 °C
8: 93 percent / Me2SO, (CF3CO)2O / CH2Cl2 / -78 °C
9: 96 percent / aluminum amalgam / H2O; tetrahydrofuran
10: DDQ / CH2Cl2; H2O / 3 h / 0 °C
11: PPTS / methanol / 1 h / 60 °C
With
dipyridinium dichromate; n-butyllithium; oxalyl dichloride; aluminium amalgam; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(96)00804-0
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 82 percent / 1.) Me2SO, (COCl)2; 2.) Et3N / CH2Cl2 / -78 °C
2: 82 percent / n-BuLi / tetrahydrofuran / -78 °C
3: 93 percent / Me2SO, (CF3CO)2O / CH2Cl2 / -78 °C
4: 96 percent / aluminum amalgam / H2O; tetrahydrofuran
5: DDQ / CH2Cl2; H2O / 3 h / 0 °C
6: PPTS / methanol / 1 h / 60 °C
With
n-butyllithium; oxalyl dichloride; aluminium amalgam; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/0040-4039(96)00804-0