Technology Process of (((4S,5R,6R)-5-(benzyloxy)-2,2-dimethyl-6-((2R,6R,7S,E)-6-methyl-7-(triisopropylsilyloxy)oct-4-en-2-yl)-1,3-dioxan-4-yl)methoxy)(tert-butyl)diphenylsilane
There total 16 articles about (((4S,5R,6R)-5-(benzyloxy)-2,2-dimethyl-6-((2R,6R,7S,E)-6-methyl-7-(triisopropylsilyloxy)oct-4-en-2-yl)-1,3-dioxan-4-yl)methoxy)(tert-butyl)diphenylsilane 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:
-
5-((R)-3-((4R,5R,6S)-5-(benzyloxy)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxan-4-yl)butylsulfonyl)-1-phenyl-1H-tetrazole;
With
potassium hexamethylsilazane;
In
tetrahydrofuran; toluene;
at -78 ℃;
for 1h;
Inert atmosphere;
(2S,3S)-2-methyl-3-(triisopropylsilyloxy)butanal;
In
tetrahydrofuran; toluene;
at -78 - 20 ℃;
chemoselective reaction;
Inert atmosphere;
DOI:10.1021/jo200396q
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: triethylamine / dichloromethane / 0.25 h / 0 °C
1.2: 12 h / 20 °C
2.1: lithium triethylborohydride / tetrahydrofuran / 5 h / 0 °C
3.1: pyridine; hydrogen fluoride / tetrahydrofuran / 10 h / 0 - 20 °C
4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C
5.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 °C / Inert atmosphere
5.2: -78 - 20 °C / Inert atmosphere
With
pyridine; hydrogen fluoride; potassium hexamethylsilazane; lithium triethylborohydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; dichloromethane; toluene;
5.1: Julia Olefin synthesis;
DOI:10.1021/jo200396q
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: lithium borohydride / tetrahydrofuran; methanol / 3 h / 0 - 20 °C
2.1: dmap; triethylamine / dichloromethane / 12 h / 0 - 20 °C
3.1: (1S)-10-camphorsulfonic acid / dichloromethane
4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 12 h / 0 °C
4.2: 2 h / 20 °C
5.1: triethylamine / dichloromethane / 0.25 h / 0 °C
5.2: 12 h / 20 °C
6.1: sodium iodide / dimethyl sulfoxide / 2 h / 90 °C
7.1: diisobutylaluminium hydride / dichloromethane / -78 °C
7.2: 0 °C
7.3: 1 h / 0 - 20 °C
8.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / 0 - 20 °C
9.1: ammonium molybdate; dihydrogen peroxide / ethanol; water / 12 h / 0 - 20 °C
10.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 °C / Inert atmosphere
10.2: -78 - 20 °C / Inert atmosphere
With
dmap; lithium borohydride; ammonium molybdate; di-isopropyl azodicarboxylate; (1S)-10-camphorsulfonic acid; dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; sodium iodide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; toluene;
4.1: Still-Barrish hydroboration / 8.1: Mitsunobu reaction / 10.1: Julia Olefin synthesis;
DOI:10.1021/jo200396q
