Technology Process of (1R,2S,3R,4S)-4-(diallylamino)cyclohex-5-ene-1,2,3-triol
There total 12 articles about (1R,2S,3R,4S)-4-(diallylamino)cyclohex-5-ene-1,2,3-triol which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
(3R,4S,5S,Z)-5-(tert-butyldimethylsilyloxy)-6,6-dimethoxy-3,4-(isopropylidenedioxy)hex-1-enylboronic acid;
With
hydrogenchloride; water;
In
tetrahydrofuran;
at 20 ℃;
for 2h;
Inert atmosphere;
diallylamine;
In
ethanol; water;
at 80 ℃;
for 192h;
diastereoselective reaction;
Inert atmosphere;
DOI:10.1021/ol203162s
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: iron(III) chloride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
2.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere
3.1: sulfuric acid / 1 h / 0 °C / Inert atmosphere
4.1: N-Bromosuccinimide; silver nitrate / acetone / 2 h / 20 °C / Inert atmosphere
5.1: pyridine; potassium diazodicarboxylate; acetic acid / methanol / 14 h / Inert atmosphere
6.1: bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine / toluene / 50 °C / Inert atmosphere
7.1: sodium periodate; ammonium acetate / water; acetone / 96 h / 20 °C / Inert atmosphere
8.1: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
8.2: 192 h / 80 °C / Inert atmosphere
With
pyridine; hydrogenchloride; iron(III) chloride; bis-triphenylphosphine-palladium(II) chloride; sodium periodate; N-Bromosuccinimide; sulfuric acid; ammonium acetate; potassium phenolate; water; potassium diazodicarboxylate; Dess-Martin periodane; silver nitrate; acetic acid; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene;
8.2: Petasis reaction;
DOI:10.1021/ol203162s
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere
2.1: sulfuric acid / 1 h / 0 °C / Inert atmosphere
3.1: N-Bromosuccinimide; silver nitrate / acetone / 2 h / 20 °C / Inert atmosphere
4.1: pyridine; potassium diazodicarboxylate; acetic acid / methanol / 14 h / Inert atmosphere
5.1: bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine / toluene / 50 °C / Inert atmosphere
6.1: sodium periodate; ammonium acetate / water; acetone / 96 h / 20 °C / Inert atmosphere
7.1: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
7.2: 192 h / 80 °C / Inert atmosphere
With
pyridine; hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; sodium periodate; N-Bromosuccinimide; sulfuric acid; ammonium acetate; potassium phenolate; water; potassium diazodicarboxylate; Dess-Martin periodane; silver nitrate; acetic acid; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene;
7.2: Petasis reaction;
DOI:10.1021/ol203162s
