Technology Process of (1R,2S,3R,4R,5R)-3-(benzyloxy)-1-ethynyl-5-methyl-2-vinylcyclohexane-1,4-diol
There total 18 articles about (1R,2S,3R,4R,5R)-3-(benzyloxy)-1-ethynyl-5-methyl-2-vinylcyclohexane-1,4-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
hydrogen fluoride;
In
acetonitrile;
at 50 ℃;
for 96h;
DOI:10.1039/c3ob40692j
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: sodium tetrahydroborate / water; tetrahydrofuran / 20 h / 0 - 20 °C
2.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C
2.2: 20 h / 20 °C
3.1: diisobutylaluminium hydride / toluene; diethyl ether / 0.25 h / -40 °C / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 20 °C
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / -10 °C
6.1: periodic acid dihydrate / diethyl ether / 0.25 h
7.1: triphenylphosphine; pyrrolidine; palladium diacetate / dimethyl sulfoxide / 20 °C
8.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere
9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C
9.2: 2 h / 20 °C
10.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere
10.2: 0.58 h / -78 - 20 °C / Inert atmosphere
11.1: potassium carbonate / methanol / 1 h / 20 °C
12.1: hydrogen fluoride / acetonitrile / 96 h / 50 °C
With
pyrrolidine; dmap; sodium tetrahydroborate; n-butyllithium; periodic acid dihydrate; hydrogen fluoride; palladium diacetate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile;
DOI:10.1039/c3ob40692j
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C
1.2: 20 h / 20 °C
2.1: diisobutylaluminium hydride / toluene; diethyl ether / 0.25 h / -40 °C / Inert atmosphere
3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 15 h / 0 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Cooling with ice
5.1: periodic acid dihydrate / diethyl ether / 0.25 h
6.1: tetrakis(triphenylphosphine) palladium(0); pyrrolidine / tetrahydrofuran / 20 °C / Inert atmosphere
7.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere
8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C
8.2: 2 h / 20 °C
9.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere
9.2: 0.58 h / -78 - 20 °C / Inert atmosphere
10.1: potassium carbonate / methanol / 1 h / 20 °C
11.1: hydrogen fluoride / acetonitrile / 96 h / 50 °C
With
pyrrolidine; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; periodic acid dihydrate; carbon tetrabromide; hydrogen fluoride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1039/c3ob40692j
