Technology Process of ethyl (12R,15R,16S,19R,20R,23R,24S)-15-[(benzyloxymeth)oxy]-12-hydroxy-16,19,24-tri(methoxymethoxy)-20,23-oxidotetratriacontanoate
There total 13 articles about ethyl (12R,15R,16S,19R,20R,23R,24S)-15-[(benzyloxymeth)oxy]-12-hydroxy-16,19,24-tri(methoxymethoxy)-20,23-oxidotetratriacontanoate 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:
-
With
C,C,C-trifluoro-N-(2-trifluoromethanesulfonylaminocyclohexyl)methanesulfonamide;
titanium(IV) isopropylate;
In
toluene;
at -20 ℃;
for 12h;
DOI:10.1021/jo981103r
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 88 percent / BF3*OEt2 / CH2Cl2 / 0.5 h / -78 °C
2: 96 percent / pyridine / 12 h
3: 88 percent / TBAF / tetrahydrofuran / 12 h / 50 °C
4: 92 percent / diisopropylethylamine / CH2Cl2 / 12 h / 20 °C
5: 97 percent / H2 / Pd-C / ethanol / 12 h
6: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
7: 90 percent / InCl3 / ethyl acetate / 2 h / -78 - 20 °C
8: 90 percent / diisopropylethylamine / CH2Cl2 / 12 h / 20 °C
9: 95 percent / H2 / Rh-Al2O3 / ethyl acetate / 4 h
10: 98 percent / TBAF / tetrahydrofuran / 2 h / 20 °C
11: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
12: 63 percent / (1S,2S)-1,2-bis(trifluoromethanesulfonamido)cyclohexane / Ti(O-i-Pr)4 / toluene / 12 h / -20 °C
With
pyridine; indium(III) chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; C,C,C-trifluoro-N-(2-trifluoromethanesulfonylaminocyclohexyl)methanesulfonamide;
titanium(IV) isopropylate; palladium on activated charcoal; rhodium on alumina;
In
tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; toluene;
1: Addition / 2: Tosylation / 3: Cyclization / 4: Etherification / 5: Catalytic hydrogenation / 6: Dess-Martin oxidation / 7: Addition / 8: Etherification / 9: Catalytic hydrogenation / 10: desilylation / 11: Dess-Martin oxidation / 12: Addition;
DOI:10.1021/jo981103r
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 88 percent / BF3*OEt2 / CH2Cl2 / 0.5 h / -78 °C
2: 96 percent / pyridine / 12 h
3: 88 percent / TBAF / tetrahydrofuran / 12 h / 50 °C
4: 92 percent / diisopropylethylamine / CH2Cl2 / 12 h / 20 °C
5: 97 percent / H2 / Pd-C / ethanol / 12 h
6: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
7: 90 percent / InCl3 / ethyl acetate / 2 h / -78 - 20 °C
8: 90 percent / diisopropylethylamine / CH2Cl2 / 12 h / 20 °C
9: 95 percent / H2 / Rh-Al2O3 / ethyl acetate / 4 h
10: 98 percent / TBAF / tetrahydrofuran / 2 h / 20 °C
11: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
12: 63 percent / (1S,2S)-1,2-bis(trifluoromethanesulfonamido)cyclohexane / Ti(O-i-Pr)4 / toluene / 12 h / -20 °C
With
pyridine; indium(III) chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; C,C,C-trifluoro-N-(2-trifluoromethanesulfonylaminocyclohexyl)methanesulfonamide;
titanium(IV) isopropylate; palladium on activated charcoal; rhodium on alumina;
In
tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; toluene;
1: Addition / 2: Tosylation / 3: Cyclization / 4: Etherification / 5: Catalytic hydrogenation / 6: Dess-Martin oxidation / 7: Addition / 8: Etherification / 9: Catalytic hydrogenation / 10: desilylation / 11: Dess-Martin oxidation / 12: Addition;
DOI:10.1021/jo981103r
