(2E)-3-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}acrylic acid methyl ester

Base Information

Chemical Name:(2E)-3-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}acrylic acid methyl ester
CAS No.:467442-93-9
Molecular Formula:C₃₀H₄₀O₃Si
Molecular Weight:476.731
Hs Code.:

Synonyms:(2E)-3-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}acrylic acid methyl ester

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Chemical Property of (2E)-3-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}acrylic acid methyl ester

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Technology Process of (2E)-3-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}acrylic acid methyl ester

There total 4 articles about (2E)-3-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}acrylic acid methyl ester 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: 94.0%

: 21204-67-1,2605-67-6
methyl (triphenylphosphoranylidene)acetate

: 392336-69-5
(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methyl-bicyclopropyl-2-carbaldehyde

: 467442-93-9
(2E)-3-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}acrylic acid methyl ester

Guidance literature:: In dichloromethane; for 28h; Heating;
DOI:10.1021/jm0105171

Reference yield:

: 111649-71-9
(E)-6-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)hex-2-en-1-ol

: 467442-93-9
(2E)-3-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / Et₂Zn; (R,R)-tartaric acid deriv.-B-n-butyl dioxaborolane / 1,2-dimethoxy-ethane; CH₂Cl₂ / 2 h / -15 °C

2: 84 percent / pyridinium chlorochromate; SiO₂ / CH₂Cl₂ / 2.5 h

3: 86 percent / CH₂Cl₂ / 19 h / Heating

4: 79 percent / DIBAL-H / hexane / 1 h / -78 °C

5: 79 percent / Et₂Zn; (R,R)-tartaric acid deriv.-B-n-butyl dioxaborolane / 1,2-dimethoxy-ethane; CH₂Cl₂ / 3 h / -15 °C

6: 92 percent / pyridinium chlorochromate; SiO₂ / CH₂Cl₂ / 1 h

7: 94 percent / CH₂Cl₂ / 28 h / Heating

With (R,R)-tartaric acid deriv.-B-n-butyl dioxaborolane; diethylzinc; silica gel; diisobutylaluminium hydride; pyridinium chlorochromate; In 1,2-dimethoxyethane; hexane; dichloromethane; 1: Charette asymmetric cyclopropanation / 3: Wittig reaction / 5: Charette asymmetric cyclopropanation / 7: Wittig reaction;
DOI:10.1021/jm0105171

Reference yield:

: 392336-21-9
(1S,2R)-2-[3-(tert-butyldiphenylsilanyloxy)propyl]cyclopropanecarbaldehyde

: 467442-93-9
(2E)-3-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / CH₂Cl₂ / 19 h / Heating

2: 79 percent / DIBAL-H / hexane / 1 h / -78 °C

3: 79 percent / Et₂Zn; (R,R)-tartaric acid deriv.-B-n-butyl dioxaborolane / 1,2-dimethoxy-ethane; CH₂Cl₂ / 3 h / -15 °C

4: 92 percent / pyridinium chlorochromate; SiO₂ / CH₂Cl₂ / 1 h

5: 94 percent / CH₂Cl₂ / 28 h / Heating

With (R,R)-tartaric acid deriv.-B-n-butyl dioxaborolane; diethylzinc; silica gel; diisobutylaluminium hydride; pyridinium chlorochromate; In 1,2-dimethoxyethane; hexane; dichloromethane; 1: Wittig reaction / 3: Charette asymmetric cyclopropanation / 5: Wittig reaction;
DOI:10.1021/jm0105171