Technology Process of 3,5-Cyclohexadiene-1,2-diol, 3-iodo-6-methyl-, (1S,2S)-
There total 1 articles about 3,5-Cyclohexadiene-1,2-diol, 3-iodo-6-methyl-, (1S,2S)- which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
water; oxygen;
Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Pseudomonas putida UV4;
DOI:10.1039/c39930000974
- Guidance literature:
-
With
hydrogen; sodium acetate;
palladium on activated charcoal;
In
methanol;
under 760 Torr;
Yield given;
Ambient temperature;
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: p-toluenesulfonic acid monohydrate / 0.25 h / 0 °C
2.1: tert.-butyl lithium; zinc(II) iodide / diethyl ether; pentane; tetrahydrofuran / 1 h / -78 - 18 °C
2.2: 18 h / 18 °C / Enzymatic reaction
3.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 20 h / 112 °C / Reflux
4.1: water / methanol / 48 h / 70 °C
5.1: dmap / pyridine / 48 h / 18 °C
6.1: dimethyl sulfoxide; oxalyl dichloride; triethylamine / dichloromethane / 0.99 h / -78 °C
7.1: samarium diiodide / tetrahydrofuran; methanol / 0.08 h / -78 °C
8.1: dichloromethane / 13 h / 18 °C / Irradiation
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C
10.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 24 h / 40 °C
11.1: water; osmium(VIII) oxide; 4-methylmorpholine N-oxide; iso-butanol / acetone / 24 h / 18 °C
With
dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; samarium diiodide; oxalyl dichloride; 2,6-di-tert-butyl-4-methyl-phenol; p-toluenesulfonic acid monohydrate; water; tert.-butyl lithium; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; iso-butanol; zinc(II) iodide; diethylazodicarboxylate;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; acetone; toluene; pentane;
2.2: |Negishi Coupling / 3.1: |Diels-Alder Cycloaddition / 6.1: |Swern Oxidation / 10.1: |Mitsunobu Displacement / 11.1: |Upjohn Dihydroxylation;
DOI:10.1021/ol5034817