Technology Process of (2S,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran
There total 12 articles about (2S,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(2S,3R,4R,5R)-(3,4-isopropylidenedioxy-5-methoxy-2-tetrahydrofuranyl)methanol;
With
sodium hydride;
In
tetrahydrofuran;
at 5 - 20 ℃;
benzyl bromide;
With
tetrahexylammonium iodide;
In
tetrahydrofuran;
at 5 - 20 ℃;
DOI:10.3987/COM-10-12001
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 - 20 °C / Inert atmosphere
3.1: 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve
3.2: 0.67 h / 5 °C
4.1: bis(benzonitrile)palladium(II) dichloride; p-benzoquinone / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
5.1: ozone / methanol / 0.5 h / -78 °C
5.2: 0 - 20 °C
6.1: sodium hydride / tetrahydrofuran / 5 - 20 °C
6.2: 5 - 20 °C
With
bis(benzonitrile)palladium(II) dichloride; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; p-benzoquinone;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.3987/COM-10-12001
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: methanol; potassium carbonate / 3 h / 20 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
2.2: -78 - 20 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere
3.2: -78 - 20 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / hexane / 1.5 h / 0 °C / Inert atmosphere
5.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 - 20 °C / Inert atmosphere
7.1: 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve
7.2: 0.67 h / 5 °C
8.1: bis(benzonitrile)palladium(II) dichloride; p-benzoquinone / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
9.1: ozone / methanol / 0.5 h / -78 °C
9.2: 0 - 20 °C
10.1: sodium hydride / tetrahydrofuran / 5 - 20 °C
10.2: 5 - 20 °C
With
methanol; bis(benzonitrile)palladium(II) dichloride; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 4-methylmorpholine N-oxide; p-benzoquinone;
In
tetrahydrofuran; methanol; hexane; dichloromethane; mineral oil;
2.1: Swern oxidation / 2.2: Swern oxidation / 3.2: Horner-Wadsworth-Emmons olefination;
DOI:10.3987/COM-10-12001
