[1,1'-Bicyclopropyl]-2-carboxaldehyde, 2'-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-2-methyl-, (1R,1'S,2S,2'S)-

Base Information

Chemical Name:[1,1'-Bicyclopropyl]-2-carboxaldehyde, 2'-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-2-methyl-, (1R,1'S,2S,2'S)-
CAS No.:392336-69-5
Molecular Formula:C27H36O2Si
Molecular Weight:420.667
Hs Code.:
Mol file:392336-69-5.mol

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Chemical Property of [1,1'-Bicyclopropyl]-2-carboxaldehyde, 2'-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-2-methyl-, (1R,1'S,2S,2'S)-

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Technology Process of [1,1'-Bicyclopropyl]-2-carboxaldehyde, 2'-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-2-methyl-, (1R,1'S,2S,2'S)-

There total 3 articles about [1,1'-Bicyclopropyl]-2-carboxaldehyde, 2'-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-2-methyl-, (1R,1'S,2S,2'S)- 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: 92.0%

: 392336-24-2
{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}methanol

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

Guidance literature:: With silica gel; pyridinium chlorochromate; In dichloromethane; for 1h;
DOI:10.1021/jm0105171

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

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;
DOI:10.1021/jm0105171

Reference yield:

: 392336-22-0
(2E)-3-{(1S,2R)-2-[3-(tert-butyldiphenylsilanyloxy)propyl]cyclopropyl}-2-methylacrylic acid ethyl ester

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

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 92 percent / pyridinium chlorochromate; SiO₂ / CH₂Cl₂ / 1 h

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