Technology Process of (3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole
There total 1 articles about (3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole 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:
-
methyl-triphenylphosphonium iodide;
With
n-butyllithium;
In
tetrahydrofuran; hexane;
at 0 - 20 ℃;
(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol;
In
tetrahydrofuran; hexane;
at -50 - 20 ℃;
for 25h;
DOI:10.1021/jo200396q
- Guidance literature:
-
With
trifluoroacetic acid;
In
water;
at 0 - 20 ℃;
for 3h;
DOI:10.1021/jo200396q
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: trifluoroacetic acid / water / 3 h / 0 - 20 °C
2.1: lithium borohydride / tetrahydrofuran; methanol / 3 h / 0 - 20 °C
3.1: dmap; triethylamine / dichloromethane / 12 h / 0 - 20 °C
4.1: (1S)-10-camphorsulfonic acid / dichloromethane
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 12 h / 0 °C
5.2: 2 h / 20 °C
6.1: triethylamine / dichloromethane / 0.25 h / 0 °C
6.2: 12 h / 20 °C
7.1: sodium iodide / dimethyl sulfoxide / 2 h / 90 °C
8.1: diisobutylaluminium hydride / dichloromethane / -78 °C
8.2: 0 °C
8.3: 1 h / 0 - 20 °C
9.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / 0 - 20 °C
10.1: ammonium molybdate; dihydrogen peroxide / ethanol; water / 12 h / 0 - 20 °C
With
dmap; lithium borohydride; ammonium molybdate; di-isopropyl azodicarboxylate; (1S)-10-camphorsulfonic acid; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; trifluoroacetic acid; sodium iodide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide;
5.1: Still-Barrish hydroboration / 9.1: Mitsunobu reaction;
DOI:10.1021/jo200396q
