Technology Process of (1R,2R,3R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-1-prop-1-ynyl-4-vinyl-cyclobutanol
There total 17 articles about (1R,2R,3R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-1-prop-1-ynyl-4-vinyl-cyclobutanol 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:
-
prop-1-yne;
With
n-butyllithium;
In
tetrahydrofuran;
at -78 - 0 ℃;
for 0.5h;
With
magnesium bromide;
at 0 ℃;
for 0.333333h;
(2R,3R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-vinyl-cyclobutanone;
In
tetrahydrofuran;
at 0 ℃;
for 2h;
Further stages.;
DOI:10.1021/ol027336t
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 19.2 g / imidozole; DMAP / CH2Cl2 / 48 h / 20 °C
2.1: zirconocene / toluene / 3 h / 20 °C
2.2: 65 percent / boron trifluoride etherate / toluene / 0.5 h / 0 °C
3.1: Dess-Martin periodinane; sodium bicarbonate / CH2Cl2 / 3 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C
4.2: MgBr2*OEt2 / 0.33 h / 0 °C
4.3: 180 mg / tetrahydrofuran / 2 h / 0 °C
With
1H-imidazole; dmap; n-butyllithium; zirconocene; sodium hydrogencarbonate; Dess-Martin periodane;
In
tetrahydrofuran; dichloromethane; toluene;
3.1: Dess-Martin oxidation / 4.2: Grignard addition;
DOI:10.1021/ol027336t
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: NaBH4
2.1: sodium hydride / tetrahydrofuran / 0 - 20 °C
2.2: 70 percent / tetra-n-butylammonium iodide / tetrahydrofuran / 3 h / 20 °C
3.1: 59 percent / aq. HCl / methanol / 0 - 20 °C
4.1: 96 percent / pyridine / 48 h / 20 °C
5.1: 87 percent / zinc; sodium iodide / dimethylformamide / Heating
6.1: 79 percent / HCl
7.1: 19.2 g / imidozole; DMAP / CH2Cl2 / 48 h / 20 °C
8.1: zirconocene / toluene / 3 h / 20 °C
8.2: 65 percent / boron trifluoride etherate / toluene / 0.5 h / 0 °C
9.1: Dess-Martin periodinane; sodium bicarbonate / CH2Cl2 / 3 h / 20 °C
10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C
10.2: MgBr2*OEt2 / 0.33 h / 0 °C
10.3: 180 mg / tetrahydrofuran / 2 h / 0 °C
With
pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; zirconocene; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; sodium iodide; zinc;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
9.1: Dess-Martin oxidation / 10.2: Grignard addition;
DOI:10.1021/ol027336t
