(1R,2R,6S)-2-[(1S,2S)-1-(hydroxymethyl)-2-methylbut-3-en-1-yl]-6-(trimethylsilyl)-3-vinylcyclohex-3-en-1-ol

Base Information

Chemical Name:(1R,2R,6S)-2-[(1S,2S)-1-(hydroxymethyl)-2-methylbut-3-en-1-yl]-6-(trimethylsilyl)-3-vinylcyclohex-3-en-1-ol
CAS No.:880145-44-8
Molecular Formula:C₁₇H₃₀O₂Si
Molecular Weight:294.51
Hs Code.:

Synonyms:(1R,2R,6S)-2-[(1S,2S)-1-(hydroxymethyl)-2-methylbut-3-en-1-yl]-6-(trimethylsilyl)-3-vinylcyclohex-3-en-1-ol

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Chemical Property of (1R,2R,6S)-2-[(1S,2S)-1-(hydroxymethyl)-2-methylbut-3-en-1-yl]-6-(trimethylsilyl)-3-vinylcyclohex-3-en-1-ol

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Technology Process of (1R,2R,6S)-2-[(1S,2S)-1-(hydroxymethyl)-2-methylbut-3-en-1-yl]-6-(trimethylsilyl)-3-vinylcyclohex-3-en-1-ol

There total 10 articles about (1R,2R,6S)-2-[(1S,2S)-1-(hydroxymethyl)-2-methylbut-3-en-1-yl]-6-(trimethylsilyl)-3-vinylcyclohex-3-en-1-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: 67.0%

: 880145-36-8
(3S,3aR,7S,7aR)-3-[(1S)-1-methylprop-2-en-1-yl]-7-(trimethylsilyl)-4-vinyl-3a,6,7,7a-tetrahydro-1-benzofuran-2(3H)-one

: 880145-44-8
(1R,2R,6S)-2-[(1S,2S)-1-(hydroxymethyl)-2-methylbut-3-en-1-yl]-6-(trimethylsilyl)-3-vinylcyclohex-3-en-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1021/ol0527328

Reference yield:

: 880145-39-1
(3S)-3-[(2R)-5-oxo-2,5-dihydrofuran-2-yl]-3-(trimethylsilyl)propanal

: 880145-44-8
(1R,2R,6S)-2-[(1S,2S)-1-(hydroxymethyl)-2-methylbut-3-en-1-yl]-6-(trimethylsilyl)-3-vinylcyclohex-3-en-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: PPh₃; Zn / CH₂Cl₂ / 24 h / 20 °C

1.2: 98 percent / CH₂Cl₂ / 48 h / 20 °C

2.1: 41 percent / n-Bu₃SnH; AIBN / ethyl acetate / 5 h / Heating

3.1: 89 percent / Pd(PPh₃)4 / dimethylformamide / 5.5 h / 57 °C

4.1: iPr₂NH; n-BuLi; HMPA / hexane; diethyl ether / -78 - 20 °C

4.2: 81 percent / aq. H₂O₂ / hexane; diethyl ether / 0.17 h / 0 °C

5.1: 85 percent / NaH / benzene / 1 h / 20 °C

6.1: 47 percent / CuBr*Me₂S / tetrahydrofuran / -40 - 20 °C

7.1: 67 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; diisopropylamine; triphenylphosphine; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene; 6.1: Michael addition;
DOI:10.1021/ol0527328

Reference yield:

: 880145-38-0
(5R)-5-[(1S)-4,4-dibromo-1-(trimethylsilyl)but-3-en-1-yl]furan-2(5H)-one

: 880145-44-8
(1R,2R,6S)-2-[(1S,2S)-1-(hydroxymethyl)-2-methylbut-3-en-1-yl]-6-(trimethylsilyl)-3-vinylcyclohex-3-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 41 percent / n-Bu₃SnH; AIBN / ethyl acetate / 5 h / Heating

2.1: 89 percent / Pd(PPh₃)4 / dimethylformamide / 5.5 h / 57 °C

3.1: iPr₂NH; n-BuLi; HMPA / hexane; diethyl ether / -78 - 20 °C

3.2: 81 percent / aq. H₂O₂ / hexane; diethyl ether / 0.17 h / 0 °C

4.1: 85 percent / NaH / benzene / 1 h / 20 °C

5.1: 47 percent / CuBr*Me₂S / tetrahydrofuran / -40 - 20 °C

6.1: 67 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; hexane; ethyl acetate; N,N-dimethyl-formamide; benzene; 5.1: Michael addition;
DOI:10.1021/ol0527328