Technology Process of (3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester
There total 7 articles about (3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
methyllithium-lithium bromide;
With
copper(l) iodide;
In
tetrahydrofuran; diethyl ether;
at -15 - 0 ℃;
for 0.5h;
(4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-5-methylhept-2-enoic acid methyl ester;
With
chloro-trimethyl-silane;
In
tetrahydrofuran; diethyl ether;
at -78 ℃;
for 3h;
DOI:10.1021/ja970251g
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: CuI / tetrahydrofuran; diethyl ether / 0.5 h / -15 - 0 °C
1.2: 92 percent / Me3SiCl / tetrahydrofuran; diethyl ether / 3 h / -78 °C
2.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C
2.2: 91 percent / Davis oxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C
3.1: 92 percent / diisopropylethylamine; DMAP / CH2Cl2 / 48 h / 0 - 20 °C
4.1: 97 percent / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 - 0 °C
5.1: oxalyl chloride; DMSO; triethylamin / CH2Cl2 / 0.83 h / -55 - -30 °C
6.1: 8.5 g / CH2Cl2 / 14 h / 20 °C
7.1: CuI / tetrahydrofuran; diethyl ether / 0.5 h / -15 - 0 °C
7.2: 85 percent / Me3SiCl / tetrahydrofuran; diethyl ether / 3 h / -78 °C
With
dmap; copper(l) iodide; oxalyl dichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene;
1.1: complexation / 1.2: Addition / 2.1: Metallation / 2.2: Oxidation / 3.1: Etherification / 4.1: Reduction / 5.1: Swern oxidation / 6.1: Wittig reaction / 7.1: complexation / 7.2: Addition;
DOI:10.1021/ja970251g
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C
1.2: 91 percent / Davis oxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C
2.1: 92 percent / diisopropylethylamine; DMAP / CH2Cl2 / 48 h / 0 - 20 °C
3.1: 97 percent / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 - 0 °C
4.1: oxalyl chloride; DMSO; triethylamin / CH2Cl2 / 0.83 h / -55 - -30 °C
5.1: 8.5 g / CH2Cl2 / 14 h / 20 °C
6.1: CuI / tetrahydrofuran; diethyl ether / 0.5 h / -15 - 0 °C
6.2: 85 percent / Me3SiCl / tetrahydrofuran; diethyl ether / 3 h / -78 °C
With
dmap; copper(l) iodide; oxalyl dichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene;
1.1: Metallation / 1.2: Oxidation / 2.1: Etherification / 3.1: Reduction / 4.1: Swern oxidation / 5.1: Wittig reaction / 6.1: complexation / 6.2: Addition;
DOI:10.1021/ja970251g
