(3S)-1-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}hex-5-en-3-ol

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Chemical Name:(3S)-1-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}hex-5-en-3-ol
CAS No.:392336-28-6
Molecular Formula:C₃₂H₄₆O₂Si
Molecular Weight:490.802
Hs Code.:

Synonyms:(3S)-1-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}hex-5-en-3-ol

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Chemical Property of (3S)-1-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}hex-5-en-3-ol

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Technology Process of (3S)-1-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}hex-5-en-3-ol

There total 4 articles about (3S)-1-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}hex-5-en-3-ol 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: 48.0%

: 106-95-6
allyl bromide

: 392336-27-5
3-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}propionaldehyde

: 392336-28-6
(3S)-1-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}hex-5-en-3-ol

Guidance literature:: allyl bromide; With (-)-B-methoxydiisopinocamphenylborane; In diethyl ether; at 20 ℃; for 1h;

3-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}propionaldehyde; In diethyl ether; at -78 ℃; for 4h; Further stages.;
DOI:10.1021/jm0105171

Reference yield:

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

: 392336-28-6
(3S)-1-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 100 percent / Et₂Zn; (R,R)-tartaric acid deriv.-B-n-butyl dioxaborolane / 1,2-dimethoxy-ethane; CH₂Cl₂ / 2 h / -15 °C

2.1: 84 percent / pyridinium chlorochromate; SiO₂ / CH₂Cl₂ / 2.5 h

3.1: 86 percent / CH₂Cl₂ / 19 h / Heating

4.1: 79 percent / DIBAL-H / hexane / 1 h / -78 °C

5.1: 79 percent / Et₂Zn; (R,R)-tartaric acid deriv.-B-n-butyl dioxaborolane / 1,2-dimethoxy-ethane; CH₂Cl₂ / 3 h / -15 °C

6.1: 92 percent / pyridinium chlorochromate; SiO₂ / CH₂Cl₂ / 1 h

7.1: 94 percent / CH₂Cl₂ / 28 h / Heating

8.1: 56 percent / NaBH₄; LiCl / ethanol; tetrahydrofuran / 19 h / 20 °C

9.1: 64 percent / pyridinium chlorochromate; SiO₂ / CH₂Cl₂ / 1.25 h

10.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1 h / 20 °C

10.2: 48 percent / diethyl ether / 4 h / -78 °C

With (-)-B-methoxydiisopinocamphenylborane; sodium tetrahydroborate; (R,R)-tartaric acid deriv.-B-n-butyl dioxaborolane; diethylzinc; silica gel; diisobutylaluminium hydride; pyridinium chlorochromate; lithium chloride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; 1.1: Charette asymmetric cyclopropanation / 3.1: Wittig reaction / 5.1: Charette asymmetric cyclopropanation / 7.1: Wittig reaction;
DOI:10.1021/jm0105171

Reference yield:

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

: 392336-28-6
(3S)-1-{(1S,2S,1'S,2'R)-2'-[3-(tert-butyldiphenylsilanyloxy)propyl]-2-methylbicyclopropyl-2-yl}hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 86 percent / CH₂Cl₂ / 19 h / Heating

2.1: 79 percent / DIBAL-H / hexane / 1 h / -78 °C

3.1: 79 percent / Et₂Zn; (R,R)-tartaric acid deriv.-B-n-butyl dioxaborolane / 1,2-dimethoxy-ethane; CH₂Cl₂ / 3 h / -15 °C

4.1: 92 percent / pyridinium chlorochromate; SiO₂ / CH₂Cl₂ / 1 h

5.1: 94 percent / CH₂Cl₂ / 28 h / Heating

6.1: 56 percent / NaBH₄; LiCl / ethanol; tetrahydrofuran / 19 h / 20 °C

7.1: 64 percent / pyridinium chlorochromate; SiO₂ / CH₂Cl₂ / 1.25 h

8.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1 h / 20 °C

8.2: 48 percent / diethyl ether / 4 h / -78 °C

With (-)-B-methoxydiisopinocamphenylborane; sodium tetrahydroborate; (R,R)-tartaric acid deriv.-B-n-butyl dioxaborolane; diethylzinc; silica gel; diisobutylaluminium hydride; pyridinium chlorochromate; lithium chloride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; 1.1: Wittig reaction / 3.1: Charette asymmetric cyclopropanation / 5.1: Wittig reaction;
DOI:10.1021/jm0105171