Technology Process of 2,2-Dimethyl-propionic acid (2S,4S,5S)-5-hydroxy-2,4-bis-(4-methoxy-benzyloxy)-3,6-dimethylene-9-trimethylsilanyl-non-8-ynyl ester
There total 10 articles about 2,2-Dimethyl-propionic acid (2S,4S,5S)-5-hydroxy-2,4-bis-(4-methoxy-benzyloxy)-3,6-dimethylene-9-trimethylsilanyl-non-8-ynyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(4-bromo-pent-4-en-1-ynyl)-trimethyl-silane;
With
tert.-butyl lithium; magnesium bromide;
In
benzene;
at -78 - 20 ℃;
for 25h;
2,2-dimethyl-propionic acid 2-(4-methoxy-benzyloxy)-3-[1-(4-methoxy-benzyloxy)-2-oxo-ethyl]-but-3-enyl ester;
With
magnesium bromide;
In
dichloromethane; benzene;
at 0 ℃;
for 0.75h;
Further stages.;
DOI:10.1021/ol0262284
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 90 percent / CSA / dimethylformamide / 38 °C
2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C
3.1: NaHMDS / 0 - 20 °C
3.2: 4 h / 0 °C
4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C
5.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C
6.1: 38 percent / CSA / 48 h / 40 °C
7.1: TBAF / tetrahydrofuran / 1.5 h
8.1: pyridine / CH2Cl2 / 0 - 20 °C
9.1: 98 percent / DMP; pyridine / CH2Cl2
10.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C
10.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C
With
pyridine; 1H-imidazole; dmap; pyridine-SO3 complex; phthalic acid dimethyl ester; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; sodium hexamethyldisilazane; N-ethyl-N,N-diisopropylamine; magnesium bromide;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
3.1: Wittig reaction / 9.1: Dess-Martin oxidation;
DOI:10.1021/ol0262284
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C
2.1: 38 percent / CSA / 48 h / 40 °C
3.1: TBAF / tetrahydrofuran / 1.5 h
4.1: pyridine / CH2Cl2 / 0 - 20 °C
5.1: 98 percent / DMP; pyridine / CH2Cl2
6.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C
6.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C
With
pyridine; 1H-imidazole; dmap; phthalic acid dimethyl ester; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; magnesium bromide;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;
5.1: Dess-Martin oxidation;
DOI:10.1021/ol0262284
