Technology Process of (1R,3S,4S,5R,6S,7S)-3-methoxy-4,6-dimethyl-7-[4-methoxybenzyloxy]-2-oxabicyclo[3.3.0]-octane
There total 7 articles about (1R,3S,4S,5R,6S,7S)-3-methoxy-4,6-dimethyl-7-[4-methoxybenzyloxy]-2-oxabicyclo[3.3.0]-octane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(1R,3S,4S,5R,6S,7S)-7-hydroxy-3-methoxy-4,6-dimethyl-2-oxabicyclo[3.3.0]-octane;
With
tetra-(n-butyl)ammonium iodide; sodium hydride;
In
tetrahydrofuran; N,N-dimethyl-formamide;
at 0 ℃;
for 0.666667h;
p-methoxybenzyl chloride;
In
tetrahydrofuran; N,N-dimethyl-formamide;
at 20 ℃;
for 40h;
Further stages.;
DOI:10.1021/ol006003y
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: LHMDS / tetrahydrofuran / 1 h / -78 °C
1.2: 86 percent / tetrahydrofuran / 1 h / -60 °C
2.1: LHMDS / tetrahydrofuran / 2 h / -78 °C
2.2: 78 percent / NH4Cl / H2O; tetrahydrofuran; diethyl ether
3.1: AcOOH; NaOAc / acetic acid / 48 h / 20 °C
4.1: 91 percent / DIBAL-H / toluene; CH2Cl2 / 3 h / -78 °C
5.1: 67 percent / Dowex-50 / 4 h / 20 °C
6.1: CuI / diethyl ether / 0.25 h / -78 - -20 °C
6.2: diethyl ether / 5 h / -30 °C
7.1: NaH; n-Bu4NI / dimethylformamide; tetrahydrofuran / 0.67 h / 0 °C
7.2: 90 percent / dimethylformamide; tetrahydrofuran / 40 h / 20 °C
With
peracetic acid; copper(l) iodide; Dowex-50; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene;
1.1: Metallation / 1.2: Methylation / 2.1: Metallation / 2.2: Protonation / 3.1: Epoxidation / 4.1: Reduction / 5.1: Etherification / 6.1: Addition / 6.2: Ring cleavage / 7.1: Reduction / 7.2: Addition;
DOI:10.1021/ol006003y
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: LHMDS / tetrahydrofuran / 2 h / -78 °C
1.2: 78 percent / NH4Cl / H2O; tetrahydrofuran; diethyl ether
2.1: AcOOH; NaOAc / acetic acid / 48 h / 20 °C
3.1: 91 percent / DIBAL-H / toluene; CH2Cl2 / 3 h / -78 °C
4.1: 67 percent / Dowex-50 / 4 h / 20 °C
5.1: CuI / diethyl ether / 0.25 h / -78 - -20 °C
5.2: diethyl ether / 5 h / -30 °C
6.1: NaH; n-Bu4NI / dimethylformamide; tetrahydrofuran / 0.67 h / 0 °C
6.2: 90 percent / dimethylformamide; tetrahydrofuran / 40 h / 20 °C
With
peracetic acid; copper(l) iodide; Dowex-50; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene;
1.1: Metallation / 1.2: Protonation / 2.1: Epoxidation / 3.1: Reduction / 4.1: Etherification / 5.1: Addition / 5.2: Ring cleavage / 6.1: Reduction / 6.2: Addition;
DOI:10.1021/ol006003y
