Technology Process of ethyl (4R,5S,6R)-4,5-dibenzyloxy-6,7-isopropylidenedioxy-2-heptenoate
There total 5 articles about ethyl (4R,5S,6R)-4,5-dibenzyloxy-6,7-isopropylidenedioxy-2-heptenoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
diethoxyphosphoryl-acetic acid ethyl ester;
With
sodium hydride;
In
tetrahydrofuran;
at 0 ℃;
for 0.75h;
(2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal;
In
tetrahydrofuran;
at -20 ℃;
for 3h;
Further stages.;
DOI:10.1021/ol0060432
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 78 percent / ZnCl2 / 24 h / 20 °C
2.1: NaH / various solvent(s); tetrahydrofuran / 2 h / 0 °C
2.2: 84 percent / tetrabutylammonium iodide / various solvent(s); tetrahydrofuran / 6 h / 20 °C
3.1: 38 percent / acetic acid; water / 3.5 h / 20 °C
4.1: 79 percent / NaIO4 / H2O; diethyl ether / 2.5 h / 20 °C
5.1: NaH / various solvent(s); tetrahydrofuran / 0.75 h / 0 °C
5.2: 89 percent / tetrahydrofuran; various solvent(s) / 3 h / -20 °C
With
sodium periodate; water; sodium hydride; acetic acid; zinc(II) chloride;
In
tetrahydrofuran; diethyl ether; water;
1.1: Addition / 2.1: Metallation / 2.2: Addition / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Metallation / 5.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol0060432
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: 38 percent / acetic acid; water / 3.5 h / 20 °C
2.1: 79 percent / NaIO4 / H2O; diethyl ether / 2.5 h / 20 °C
3.1: NaH / various solvent(s); tetrahydrofuran / 0.75 h / 0 °C
3.2: 89 percent / tetrahydrofuran; various solvent(s) / 3 h / -20 °C
With
sodium periodate; water; sodium hydride; acetic acid;
In
tetrahydrofuran; diethyl ether; water;
1.1: Hydrolysis / 2.1: Oxidation / 3.1: Metallation / 3.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol0060432
