Technology Process of (+)-5-ethenyl-3-methylcyclohex-5-en-1,3-diol
There total 10 articles about (+)-5-ethenyl-3-methylcyclohex-5-en-1,3-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: AD-mix-α; water; methanesulfonamide / tert-butyl alcohol / 14 h / 0 °C
2.1: pyridine / 3 h / 0 °C
3.1: dimethyl sulfoxide / 16 h / Inert atmosphere
4.1: collidine / dichloromethane / 12 h / 0 °C
5.1: ammonium cerium (IV) nitrate / acetonitrile; water / 0.08 h / 0 °C
6.1: Dess-Martin periodane / dichloromethane / 8 h / 20 °C / Inert atmosphere
7.1: tetrahydrofuran; toluene / 2 h / -78 - 20 °C / Inert atmosphere
8.1: Grubbs catalyst first generation / dichloromethane / 24 h / Inert atmosphere
8.2: 16 h
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 °C
With
pyridine; Grubbs catalyst first generation; ammonium cerium (IV) nitrate; methanesulfonamide; AD-mix-α; tetrabutyl ammonium fluoride; water; Dess-Martin periodane;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; tert-butyl alcohol;
1.1: |Sharpless Dihydroxylation / 6.1: |Dess-Martin Oxidation;
DOI:10.1002/ejoc.201301627
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / 0 - 20 °C
2.1: AD-mix-α; water; methanesulfonamide / tert-butyl alcohol / 14 h / 0 °C
3.1: pyridine / 3 h / 0 °C
4.1: dimethyl sulfoxide / 16 h / Inert atmosphere
5.1: collidine / dichloromethane / 12 h / 0 °C
6.1: ammonium cerium (IV) nitrate / acetonitrile; water / 0.08 h / 0 °C
7.1: Dess-Martin periodane / dichloromethane / 8 h / 20 °C / Inert atmosphere
8.1: tetrahydrofuran; toluene / 2 h / -78 - 20 °C / Inert atmosphere
9.1: Grubbs catalyst first generation / dichloromethane / 24 h / Inert atmosphere
9.2: 16 h
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 °C
With
pyridine; Grubbs catalyst first generation; ammonium cerium (IV) nitrate; methanesulfonamide; AD-mix-α; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; triphenylphosphine;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; tert-butyl alcohol;
2.1: |Sharpless Dihydroxylation / 7.1: |Dess-Martin Oxidation;
DOI:10.1002/ejoc.201301627