(3R,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

Base Information

Chemical Name:(3R,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene
CAS No.:146728-45-2
Molecular Formula:C₂₁H₄₀O₂Si₂
Molecular Weight:380.718
Hs Code.:

Synonyms:(3R,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

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Chemical Property of (3R,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

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Technology Process of (3R,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

There total 13 articles about (3R,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene 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:

: 146728-46-3
(1R,2S,4R,6R)-2-Ethenyl-2-hydroxy-4-isopropenyl-1-methyl-7-oxabicyclo<4.1.0>heptane

: 146728-45-2
(3R,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / 4-dimethylaminopyridine, NEt₃

2: 1) ozone 2) p-nitrobenzoyl chloride, pyridine / 1) CH₂Cl₂, MeOH, -78 deg C, 2) CH₂Cl₂

3: SmI₂ / Pd(PPh₃)4

4: NaOMe / methanol / 0 °C

5: imidazole / dimethylformamide

With pyridine; 1H-imidazole; dmap; samarium diiodide; sodium methylate; 4-nitro-benzoyl chloride; ozone; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00059a048

Reference yield:

: (1R,2S,4R,6R)-2-Acetoxy-2-ethenyl-4-isopropenyl-1-methyl-7-oxabicyclo<4.1.0>heptane

: 146728-45-2
(3R,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

Guidance literature:: Multi-step reaction with 4 steps

1: 1) ozone 2) p-nitrobenzoyl chloride, pyridine / 1) CH₂Cl₂, MeOH, -78 deg C, 2) CH₂Cl₂

2: SmI₂ / Pd(PPh₃)4

3: NaOMe / methanol / 0 °C

4: imidazole / dimethylformamide

With pyridine; 1H-imidazole; samarium diiodide; sodium methylate; 4-nitro-benzoyl chloride; ozone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00059a048

Reference yield:

: (1R,2S,4R,6R)-2,4-Diacetoxy-2-ethynyl-1-methyl-7-oxa-bicyclo<4.1.0>heptane

: 146728-45-2
(3R,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

Guidance literature:: Multi-step reaction with 3 steps

1: SmI₂ / Pd(PPh₃)4

2: NaOMe / methanol / 0 °C

3: imidazole / dimethylformamide

With 1H-imidazole; samarium diiodide; sodium methylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00059a048