Technology Process of (1R,3R,4R, 8S)-1-benzoyloxymethyl-8-benzyloxy-3-(thymin-1-yl)-2,6-dioxabicyclo[3,2,1]octane
There total 13 articles about (1R,3R,4R, 8S)-1-benzoyloxymethyl-8-benzyloxy-3-(thymin-1-yl)-2,6-dioxabicyclo[3,2,1]octane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
1-[3-O-benzyl-4-C-hydroxymethyl-2-deoxy-2-acetoxymethyl-3-β-ribo-pentofuranosyl]thymine;
With
pyridine; methanesulfonyl chloride;
at 20 ℃;
Inert atmosphere;
With
sodium hydroxide;
In
1,4-dioxane; water;
at 20 - 60 ℃;
for 1.33333h;
sodium benzoate;
In
N,N-dimethyl-formamide;
at 130 ℃;
for 5h;
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: p-toluenesulfonic acid monohydrate; sodium iodide / acetone / 4 h / 55 °C
2.1: pyridine / 20 °C / Inert atmosphere
3.1: triethylamine; dmap / toluene / 1.17 h / 20 °C / Inert atmosphere
4.1: 2,2'-azobis(isobutyronitrile); hexamethyldistannane / benzene / 5 h / Reflux
4.2: 1 h / 20 °C
5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / -10 °C / Inert atmosphere; Cooling with ice
5.2: 19 h / -10 - 4 °C
6.1: hydrogenchloride / ethyl acetate / 2 h / 0 °C / Cooling with ice
7.1: Dess-Martin periodane / dichloromethane / 2.5 h / 0 °C
7.2: 15 h
8.1: pyridine / 3 h / 20 °C / Inert atmosphere
9.1: ozone / dichloromethane / 1 h / -78 °C / Cooling with acetone-dry ice
9.2: 0.33 h / 0 - 20 °C
10.1: pyridine / 20 °C / Inert atmosphere
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere
12.1: pyridine; methanesulfonyl chloride / 20 °C / Inert atmosphere
12.2: 1.33 h / 20 - 60 °C
12.3: 5 h / 130 °C
With
pyridine; hydrogenchloride; dmap; 2,2'-azobis(isobutyronitrile); p-toluenesulfonic acid monohydrate; tetrabutyl ammonium fluoride; hexamethyldistannane; sodium hydride; Dess-Martin periodane; ozone; methanesulfonyl chloride; triethylamine; sodium iodide;
In
tetrahydrofuran; pyridine; dichloromethane; ethyl acetate; acetone; toluene; mineral oil; benzene;
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: triethylamine; dmap / toluene / 1.17 h / 20 °C / Inert atmosphere
2.1: 2,2'-azobis(isobutyronitrile); hexamethyldistannane / benzene / 5 h / Reflux
2.2: 1 h / 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / -10 °C / Inert atmosphere; Cooling with ice
3.2: 19 h / -10 - 4 °C
4.1: hydrogenchloride / ethyl acetate / 2 h / 0 °C / Cooling with ice
5.1: Dess-Martin periodane / dichloromethane / 2.5 h / 0 °C
5.2: 15 h
6.1: pyridine / 3 h / 20 °C / Inert atmosphere
7.1: ozone / dichloromethane / 1 h / -78 °C / Cooling with acetone-dry ice
7.2: 0.33 h / 0 - 20 °C
8.1: pyridine / 20 °C / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere
10.1: pyridine; methanesulfonyl chloride / 20 °C / Inert atmosphere
10.2: 1.33 h / 20 - 60 °C
10.3: 5 h / 130 °C
With
pyridine; hydrogenchloride; dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hexamethyldistannane; sodium hydride; Dess-Martin periodane; ozone; methanesulfonyl chloride; triethylamine;
In
tetrahydrofuran; pyridine; dichloromethane; ethyl acetate; toluene; mineral oil; benzene;
