Technology Process of Acetic acid (3S,6S,8aS)-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-5-oxo-octahydro-indolizin-6-yl ester
There total 9 articles about Acetic acid (3S,6S,8aS)-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-5-oxo-octahydro-indolizin-6-yl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 96 percent / H2 / 10 percent Pd/C / ethyl acetate
2.1: 71 percent / B-bromocatecholborane / CH2Cl2
3.1: 98 percent / NaOMe / methanol
4.1: 86 percent / Bu4NI / tetrahydrofuran
5.1: 97 percent / t-BuLi / tetrahydrofuran / -78 °C
6.1: 64 percent / t-BuLi; (MeO)3P; O2 / tetrahydrofuran / -78 °C
7.1: 84 percent / DDQ / CH2Cl2; H2O
8.1: NaH; CS2; MeI / tetrahydrofuran
8.2: 67 percent / Ph3SnH; AIBN / toluene / 0.5 h / Heating
9.1: 92 percent / Pyr; DMAP
With
pyridine; carbon disulfide; dmap; bromocatecholborane; hydrogen; tert.-butyl lithium; oxygen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; phosphorous acid trimethyl ester; methyl iodide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate;
1.1: Catalytic hydrogenation / 2.1: Decarboxylation / 3.1: lactam formation / 4.1: Etherification / 5.1: Methylation / 6.1: hydroxylation / 7.1: deprotection / 8.1: deoxygenation / 8.2: deoxygenation / 9.1: Acetylation;
DOI:10.1016/S0960-894X(99)00669-1
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 98 percent / NaOMe / methanol
2.1: 86 percent / Bu4NI / tetrahydrofuran
3.1: 97 percent / t-BuLi / tetrahydrofuran / -78 °C
4.1: 64 percent / t-BuLi; (MeO)3P; O2 / tetrahydrofuran / -78 °C
5.1: 84 percent / DDQ / CH2Cl2; H2O
6.1: NaH; CS2; MeI / tetrahydrofuran
6.2: 67 percent / Ph3SnH; AIBN / toluene / 0.5 h / Heating
7.1: 92 percent / Pyr; DMAP
With
pyridine; carbon disulfide; dmap; tert.-butyl lithium; oxygen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; phosphorous acid trimethyl ester; methyl iodide;
In
tetrahydrofuran; methanol; dichloromethane; water;
1.1: lactam formation / 2.1: Etherification / 3.1: Methylation / 4.1: hydroxylation / 5.1: deprotection / 6.1: deoxygenation / 6.2: deoxygenation / 7.1: Acetylation;
DOI:10.1016/S0960-894X(99)00669-1