(1R,2R,3R,4R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-1-(2-trimethylsilylethynyl)-4-vinylcyclobutanol

Base Information

Chemical Name:(1R,2R,3R,4R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-1-(2-trimethylsilylethynyl)-4-vinylcyclobutanol
CAS No.:500187-76-8
Molecular Formula:C₂₅H₄₀O₄Si₂
Molecular Weight:460.761
Hs Code.:

Synonyms:(1R,2R,3R,4R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-1-(2-trimethylsilylethynyl)-4-vinylcyclobutanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,2R,3R,4R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-1-(2-trimethylsilylethynyl)-4-vinylcyclobutanol

Chemical Property:

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Useful:

Technology Process of (1R,2R,3R,4R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-1-(2-trimethylsilylethynyl)-4-vinylcyclobutanol

There total 25 articles about (1R,2R,3R,4R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-1-(2-trimethylsilylethynyl)-4-vinylcyclobutanol 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:

Reference yield:

: 1066-54-2
trimethylsilylacetylene

: (2R,3R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-vinyl-cyclobutanone

: 500187-76-8
(1R,2R,3R,4R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-1-(2-trimethylsilylethynyl)-4-vinylcyclobutanol

Guidance literature:: trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃;

With magnesium bromide; at 0 ℃; for 0.5h;

(2R,3R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-vinyl-cyclobutanone; In tetrahydrofuran; at 0 ℃; for 3h; Further stages.;
DOI:10.1021/ol027336t

Reference yield:

: 205934-53-8
(3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole

: 500187-76-8
(1R,2R,3R,4R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-1-(2-trimethylsilylethynyl)-4-vinylcyclobutanol

Guidance literature:: Multi-step reaction with 5 steps

1: 79 percent / HCl / methanol / 0 °C

2: 88 percent / imidazole; DMAP / CH₂Cl₂ / 48 h / 20 °C

3: 65 percent / zirconocene dichloride; n-butyllithium; boron trifluoride etherate / toluene / 3 h / 20 °C

4: sodium bicarbonate / CH₂Cl₂ / 3 h / 20 °C

5: 118 mg / tetrahydrofuran / 3 h / 0 °C

With 1H-imidazole; hydrogenchloride; dmap; n-butyllithium; zirconocene dichloride; boron trifluoride diethyl etherate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; toluene; 4: Dess-Martin oxidation;
DOI:10.1021/jo051989g

Reference yield:

: (2S,4R,5R)-2-Methoxy-4-(4-methoxy-benzyloxy)-5-vinyl-dihydro-furan-3-one

: 500187-76-8
(1R,2R,3R,4R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-1-(2-trimethylsilylethynyl)-4-vinylcyclobutanol

Guidance literature:: Multi-step reaction with 7 steps

1: 94 mg / sodium borohydride / methanol / 0.5 h / 0 °C

2: 87 percent / imidazole; DMAP / CH₂Cl₂ / 48 h / 20 °C

3: HCl / methanol / 20 °C

4: 345 mg / imidazole; DMAP / CH₂Cl₂ / 48 h / 20 °C

5: 65 percent / zirconocene dichloride; n-butyllithium; boron trifluoride etherate / toluene / 3 h / 20 °C

6: sodium bicarbonate / CH₂Cl₂ / 3 h / 20 °C

7: 118 mg / tetrahydrofuran / 3 h / 0 °C

With 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; zirconocene dichloride; boron trifluoride diethyl etherate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; toluene; 6: Dess-Martin oxidation;
DOI:10.1021/jo051989g