Technology Process of (1S,2R,5S,6S)-2-(2,3-Dimethoxy-phenyl)-6-methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-ol
There total 1 articles about (1S,2R,5S,6S)-2-(2,3-Dimethoxy-phenyl)-6-methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-ol 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:
-
1,2-dimethoxybenzene;
With
n-butyllithium;
at -78 ℃;
(1S,5S,6S)-6-Methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-one;
In
tetrahydrofuran;
at -78 ℃;
DOI:10.1039/b101668g
- Guidance literature:
-
With
pyridinium chlorochromate;
In
dichloromethane;
DOI:10.1039/b101668g
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: PCC / CH2Cl2
2.1: 75 percent / CuBr*Me2S / hexamethylphosphoric acid triamide; tetrahydrofuran
3.1: NBS / CH2Cl2 / 20 °C
4.1: 82 percent / dimethylformamide / 0.5 h / Heating
5.1: 71 percent / TfOTMS / CH2Cl2
6.1: BH3-Me2S
6.2: 72 percent / aq. H2O2; NaOH
7.1: 87 percent / pyridine
8.1: 50 percent / (CH2OH)2; p-TsOH / benzene / 15 h / Heating
9.1: 100 percent / LiAlH4 / tetrahydrofuran / 20 °C
10.1: 1,1'-(azodicarbonyl)dipiperidine; Bu3P / tetrahydrofuran
With
pyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; copper(I) bromide dimethylsulfide complex; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; toluene-4-sulfonic acid; ethylene glycol; pyridinium chlorochromate; 1,1'-azodicarbonyl-dipiperidine;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; benzene;
10.1: Mitsunobu reaction;
DOI:10.1039/b101668g
