Technology Process of (1S)-cis-4-Benzyloxymethylcyclopent-2-en-1-ol
There total 6 articles about (1S)-cis-4-Benzyloxymethylcyclopent-2-en-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Benzyloxymethyl chloride;
With
bromine; magnesium; mercury dichloride;
In
tetrahydrofuran;
at -5 ℃;
for 2.5h;
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate;
In
tetrahydrofuran;
at -20 ℃;
for 0.25h;
Further stages.;
DOI:10.1055/s-2007-967937
- Guidance literature:
-
[(1S)-trans-1-(4-Benzyloxymethylcyclopent-2-en-1-yloxy)ethenyloxy] tert-butyldimethylsilane;
In
xylene;
at 190 ℃;
for 18h;
With
sodium hydroxide; water;
In
tetrahydrofuran;
for 2h;
DOI:10.1039/a907522d
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: NaH / dimethylformamide / 0.25 h / 0 °C
1.2: 81 percent / dimethylformamide / 17 h / -60 - 20 °C
2.1: 87 percent / DEAD; Ph3P / diethyl ether / 17 h / -10 - 25 °C
3.1: LDA / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 0.33 h / -78 °C
3.2: 100 percent / hexane; tetrahydrofuran / 0.42 h / -78 - 20 °C
4.1: xylene / 18 h / 190 °C
4.2: 33 percent / NaOH; H2O / tetrahydrofuran / 2 h
With
sodium hydride; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; N,N-dimethyl-formamide; xylene;
1.1: Metallation / 1.2: Etherification / 2.1: Acetylation / 3.1: Metallation / 3.2: Etherification / 4.1: Rearrangement / 4.2: Hydrolysis;
DOI:10.1039/a907522d
