Technology Process of (1R,2R,3S,6R)-6-(acetoxymethyl)cyclohex-4-ene-1,2,3-triyl triacetate
There total 15 articles about (1R,2R,3S,6R)-6-(acetoxymethyl)cyclohex-4-ene-1,2,3-triyl triacetate 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:
-
(1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate;
With
tributylphosphine;
In
dichloromethane;
at 20 ℃;
for 1h;
With
acetic anhydride; triethylamine;
In
dichloromethane;
at -78 - 20 ℃;
DOI:10.1002/ejoc.201100956
- Guidance literature:
-
(1S)-(1,3/2,4)-1,2-dibenzyloxy-3-hydroxy-4-hydroxymethylcyclohex-5-ene;
With
ammonia; lithium;
In
tetrahydrofuran;
at -60 ℃;
acetic anhydride;
With
pyridine;
at 20 ℃;
DOI:10.1002/ejoc.201701601
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: dipyridinium dichromate; acetic anhydride / dichloromethane / 16 h / 20 °C
2.1: diethyl ether / 6 h / 0 - 20 °C / Inert atmosphere
3.1: potassium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere
4.1: acetic acid / tetrahydrofuran; water / 5 h / Heating
5.1: pyridine / 24 h
6.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 6 h / 85 °C / Inert atmosphere
6.2: 10 h / Heating
7.1: ozone / methanol / -78 °C
7.2: -78 - 20 °C
8.1: dimethylsulfide borane complex / tetrahydrofuran / 1 h / 0 - 20 °C
9.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C
10.1: sodium azide / N,N-dimethyl-formamide / 48 h / 85 °C
11.1: tributylphosphine / dichloromethane / 1 h / 20 °C
11.2: -78 - 20 °C
With
dipyridinium dichromate; sodium azide; 2,2'-azobis(isobutyronitrile); tributylphosphine; dimethylsulfide borane complex; tri-n-butyl-tin hydride; acetic anhydride; potassium hydride; ozone; acetic acid; triethylamine;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;
3.1: Peterson olefination;
DOI:10.1002/ejoc.201100956
