<3aR-<3aα,4α(1E,3R^*),5β,6aα>>-(1,1-dimethylethyl)<<1-<2-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-(dimethylphenylsilyl)-2-methylene-4-octahydropentalenyl>ethenyl>hexyl>oxy>dimethylsilane

Base Information

• Chemical Name: <3aR-<3aα,4α(1E,3R^*),5β,6aα>>-(1,1-dimethylethyl)<<1-<2-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-(dimethylphenylsilyl)-2-methylene-4-octahydropentalenyl>ethenyl>hexyl>oxy>dimethylsilane
• CAS No.: 111005-08-4
• Molecular Formula: C₃₇H₆₆O₂Si₃
• Molecular Weight: 627.186

Synonyms:<3aR-<3aα,4α(1E,3R^*),5β,6aα>>-(1,1-dimethylethyl)<<1-<2-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-(dimethylphenylsilyl)-2-methylene-4-octahydropentalenyl>ethenyl>hexyl>oxy>dimethylsilane

Chemical Property of <3aR-<3aα,4α(1E,3R^*),5β,6aα>>-(1,1-dimethylethyl)<<1-<2-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-(dimethylphenylsilyl)-2-methylene-4-octahydropentalenyl>ethenyl>hexyl>oxy>dimethylsilane

Chemical Property:

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Technology Process of <3aR-<3aα,4α(1E,3R^*),5β,6aα>>-(1,1-dimethylethyl)<<1-<2-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-(dimethylphenylsilyl)-2-methylene-4-octahydropentalenyl>ethenyl>hexyl>oxy>dimethylsilane

There total 8 articles about <3aR-<3aα,4α(1E,3R^*),5β,6aα>>-(1,1-dimethylethyl)<<1-<2-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-(dimethylphenylsilyl)-2-methylene-4-octahydropentalenyl>ethenyl>hexyl>oxy>dimethylsilane 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: 79.0%

<1S-<1α,2α,3β(1E,3R*),4α>>-O-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-<3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-octenyl>-2-(2-propynyl)cyclopentyl>(dimethylphenylsilyl)methyl S-methyl carbonodithioate (110972-11-7) → <3aR-<3aα,4α(1E,3R*),5β,6aα>>-(1,1-dimethylethyl)<<1-<2-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-(dimethylphenylsilyl)-2-methylene-4-octahydropentalenyl>ethenyl>hexyl>oxy>dimethylsilane (111005-08-4)

Guidance literature:

With di-tert-butyl peroxide; tri-n-butyl-tin hydride; In benzene; at 75 ℃; for 36h;

DOI:10.1021/jo00234a014

Reference yield: 50.0%

<1S-<1α,2α,3β(1E,3R*),4α>>-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-<3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-octenyl>-2-(2-propynyl)cyclopentyl>(dimethylphenylsilyl)methyl m-(trifluoromethyl)benzoate → <3aR-<3aα,4α(1E,3R*),5β,6aα>>-(1,1-dimethylethyl)<<1-<2-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-(dimethylphenylsilyl)-2-methylene-4-octahydropentalenyl>ethenyl>hexyl>oxy>dimethylsilane (111005-08-4)

Guidance literature:

With magnesium(II) perchlorate; N-methylcarbazole; In tetrahydrofuran; water; at 20 ℃; for 4h; Irradiation;

DOI:10.1021/jo00234a014

Reference yield:

(1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene (41138-67-4) → <3aR-<3aα,4α(1E,3R*),5β,6aα>>-(1,1-dimethylethyl)<<1-<2-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-(dimethylphenylsilyl)-2-methylene-4-octahydropentalenyl>ethenyl>hexyl>oxy>dimethylsilane (111005-08-4)

Guidance literature:

Multi-step reaction with 6 steps

2: 78 percent / Zn, TiCl₄ / CH₂Cl₂ / 1 h / 0 °C

3: 1.) 9-borabicyclo<3.3.1>nonane, 2.) aq. NaOH, H₂O₂ / 1.) THF, from 0 to 18 deg C, 3 h, 2.) THF, 0 deg C, 15 min

4: 95 percent / oxalyl chloride, DMSO, triethylamine / CH₂Cl₂ / 1.) -50 deg C, 10 min, 2.) 17 deg C, 1 h

5: 1.) THF, -78 deg C, 5 min, 2.) THF, HMPA, 0 deg C, 60 min

6: 50 percent / Mg(ClO₄)2, N-methylcarbazole / tetrahydrofuran; H₂O / 4 h / 20 °C / Irradiation

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; magnesium(II) perchlorate; N-methylcarbazole; oxalyl dichloride; dihydrogen peroxide; titanium tetrachloride; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00234a014

upstream raw materials:

<1S-<1α,2α,3β(1E,3R^*),4α>>-O-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-<3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-octenyl>-2-(2-propynyl)cyclopentyl>(dimethylphenylsilyl)methyl S-methyl carbonodithioate

(1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene

<2S-<1α,2α,3β,(1E,3R^*),4α>>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-<3-<(1,1-dimethylethyl)dimrthylsilyl>oxy-1-octenyl>-2-(2-propynyl)cyclopentanemethanol

<1S-<1α,2α,3β(1E,3R^*),4α>>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-<3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-octenyl>-2-(2-propynyl)cyclopentanecarboxaldehyde

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