Technology Process of (4R,5R,7R,8S)-4,8-bis(benzyloxy)-5,9-bis(t-butyldimethylsiloxy)-2,2-dichloro-7-(4-methoxybenzyloxy)-6,6-dimethylnonan-3-one
There total 17 articles about (4R,5R,7R,8S)-4,8-bis(benzyloxy)-5,9-bis(t-butyldimethylsiloxy)-2,2-dichloro-7-(4-methoxybenzyloxy)-6,6-dimethylnonan-3-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
n-butyllithium;
In
tetrahydrofuran; diethyl ether; hexane;
at -100 - -78 ℃;
for 1h;
DOI:10.1246/bcsj.74.113
- Guidance literature:
-
Multi-step reaction with 3 steps
1: 87 percent / MgBr2*Et2O / toluene / 1 h / -19 °C
2: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
3: 78 percent / n-BuLi / hexane; diethyl ether; tetrahydrofuran / 1 h / -100 - -78 °C
With
2,6-dimethylpyridine; n-butyllithium; magnesium bromide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1246/bcsj.74.113
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: camphorsulfonic acid / CH2Cl2 / 2 h / 20 °C
1.2: 92 percent / Et3N / CH2Cl2
2.1: 21.2 g / oxalyl chloride; DMSO / CH2Cl2 / -78 - 20 °C
3.1: 86 percent / n-BuLi / hexane; tetrahydrofuran / -15 - 20 °C
4.1: OsO4; N-methylmorpholine-N-oxide / H2O; acetone; 2-methyl-propan-2-ol / 72 h / 2 °C
5.1: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C
6.1: 96 percent / NaH / tetrahydrofuran; dimethylformamide / 18 h / 0 - 20 °C
7.1: 85 percent / BH3*Me2S / toluene / 0.5 h / Heating
8.1: 67 percent / oxalyl chloride; DMSO / CH2Cl2 / -78 - 20 °C
9.1: 87 percent / MgBr2*Et2O / toluene / 1 h / -19 °C
10.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
11.1: 78 percent / n-BuLi / hexane; diethyl ether; tetrahydrofuran / 1 h / -100 - -78 °C
With
1H-imidazole; 2,6-dimethylpyridine; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; camphor-10-sulfonic acid; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; magnesium bromide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
2.1: Swern's oxidation / 3.1: Wittig reaction / 8.1: Swern's oxidation;
DOI:10.1246/bcsj.74.113
