Technology Process of (4S,5R,6R,7R,9Z)-6-[(tert-butyldimethylsilyl)oxy]-11-[(4-methoxyphenyl)methoxy]-5,7-dimethylundec-9-en-1-yn-4-ol
There total 8 articles about (4S,5R,6R,7R,9Z)-6-[(tert-butyldimethylsilyl)oxy]-11-[(4-methoxyphenyl)methoxy]-5,7-dimethylundec-9-en-1-yn-4-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:
-
propargyl bromide;
With
pyridine; indium; (1S,2R)-2-Amino-1,2-diphenylethanol;
In
tetrahydrofuran; toluene;
at -20 ℃;
for 0.75h;
Inert atmosphere;
(2S,3R,4R,Z)-3-((tert-butyldimethylsilyl)oxy)-8-((4-methoxybenzyl)oxy)-2,4-dimethyloct-6-enal;
In
tetrahydrofuran; toluene;
for 16h;
optical yield given as %de;
diastereoselective reaction;
Inert atmosphere;
DOI:10.1021/jo300225z
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: toluene-4-sulfonic acid / methanol / 2 h / 0 - 20 °C / Inert atmosphere
2.1: quinoline; hydrogen / ethyl acetate / 2 h
3.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere
4.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere
4.2: 3 h / -78 °C / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere
6.1: lithium borohydride / methanol; dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere
7.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere
8.1: pyridine; indium; (1S,2R)-2-Amino-1,2-diphenylethanol / tetrahydrofuran; toluene / 0.75 h / -20 °C / Inert atmosphere
8.2: 16 h / Inert atmosphere
With
pyridine; quinoline; indium; lithium borohydride; (1S,2R)-2-Amino-1,2-diphenylethanol; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
3.1: Swern oxidation / 4.1: Evans aldol reaction / 4.2: Evans aldol reaction / 7.1: Swern oxidation / 8.1: Barbier reaction / 8.2: Barbier reaction;
DOI:10.1021/jo300225z
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere
1.2: 3 h / -78 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere
3.1: lithium borohydride / methanol; dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere
4.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere
5.1: pyridine; indium; (1S,2R)-2-Amino-1,2-diphenylethanol / tetrahydrofuran; toluene / 0.75 h / -20 °C / Inert atmosphere
5.2: 16 h / Inert atmosphere
With
pyridine; indium; lithium borohydride; (1S,2R)-2-Amino-1,2-diphenylethanol; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; dichloromethane; toluene;
1.1: Evans aldol reaction / 1.2: Evans aldol reaction / 4.1: Swern oxidation / 5.1: Barbier reaction / 5.2: Barbier reaction;
DOI:10.1021/jo300225z
