(1S,4S,5S)-2-(phenylsulfenyl)-5-((tert-butyldimethylsilyl)oxy)bicyclo<2.2.2>oct-2-ene

Base Information

Chemical Name:(1S,4S,5S)-2-(phenylsulfenyl)-5-((tert-butyldimethylsilyl)oxy)bicyclo<2.2.2>oct-2-ene
CAS No.:177748-76-4
Molecular Formula:C₂₀H₃₀OSSi
Molecular Weight:346.609
Hs Code.:

Synonyms:(1S,4S,5S)-2-(phenylsulfenyl)-5-((tert-butyldimethylsilyl)oxy)bicyclo<2.2.2>oct-2-ene

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Chemical Property of (1S,4S,5S)-2-(phenylsulfenyl)-5-((tert-butyldimethylsilyl)oxy)bicyclo<2.2.2>oct-2-ene

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Technology Process of (1S,4S,5S)-2-(phenylsulfenyl)-5-((tert-butyldimethylsilyl)oxy)bicyclo<2.2.2>oct-2-ene

There total 6 articles about (1S,4S,5S)-2-(phenylsulfenyl)-5-((tert-butyldimethylsilyl)oxy)bicyclo<2.2.2>oct-2-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: 49.0%

: Methanesulfonic acid (1R,4S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-3-phenylsulfanyl-bicyclo[2.2.2]oct-2-yl ester

: 177748-76-4
(1S,4S,5S)-2-(phenylsulfenyl)-5-((tert-butyldimethylsilyl)oxy)bicyclo<2.2.2>oct-2-ene

Guidance literature:: With potassium tert-butylate; In 1,2-dimethoxyethane; at -40 ℃; for 2h;
DOI:10.1021/jo9601167

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 177748-76-4
(1S,4S,5S)-2-(phenylsulfenyl)-5-((tert-butyldimethylsilyl)oxy)bicyclo<2.2.2>oct-2-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

2: 93 percent / LDA / tetrahydrofuran / 1.) -78 - room temperature, 2 h, 2.) room temperature, 30 min

3: 2.) NaBH₄ / 1.) CH₂Cl₂, -78 deg C, 45 min, room temperature, 30 min, 2.) THF, -78 deg C, 24 h

4: 90 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / 40 °C

5: 49 percent / potassium tert-butoxide / 1,2-dimethoxy-ethane / 2 h / -40 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; potassium tert-butylate; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo9601167

Reference yield:

: 129100-39-6
(1R,4S,6S)-bicyclo<2.2.2>octane-6-ol-2-one

: 177748-76-4
(1S,4S,5S)-2-(phenylsulfenyl)-5-((tert-butyldimethylsilyl)oxy)bicyclo<2.2.2>oct-2-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

2: 93 percent / LDA / tetrahydrofuran / 1.) -78 - room temperature, 2 h, 2.) room temperature, 30 min

3: 2.) NaBH₄ / 1.) CH₂Cl₂, -78 deg C, 45 min, room temperature, 30 min, 2.) THF, -78 deg C, 24 h

4: 90 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / 40 °C

5: 49 percent / potassium tert-butoxide / 1,2-dimethoxy-ethane / 2 h / -40 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; potassium tert-butylate; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo9601167