rel-(1R,5S,6R,8S)-6-acetoxy-8-((1S)-1-acetoxy-2-p-toluenesulfonyloxyethyl)bicyclo(3.3.0)octan-3-one

Base Information

Chemical Name:rel-(1R,5S,6R,8S)-6-acetoxy-8-((1S)-1-acetoxy-2-p-toluenesulfonyloxyethyl)bicyclo(3.3.0)octan-3-one
CAS No.:109387-12-4
Molecular Formula:C₂₁H₂₆O₈S
Molecular Weight:438.499
Hs Code.:

Synonyms:rel-(1R,5S,6R,8S)-6-acetoxy-8-((1S)-1-acetoxy-2-p-toluenesulfonyloxyethyl)bicyclo(3.3.0)octan-3-one

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Chemical Property of rel-(1R,5S,6R,8S)-6-acetoxy-8-((1S)-1-acetoxy-2-p-toluenesulfonyloxyethyl)bicyclo(3.3.0)octan-3-one

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Technology Process of rel-(1R,5S,6R,8S)-6-acetoxy-8-((1S)-1-acetoxy-2-p-toluenesulfonyloxyethyl)bicyclo(3.3.0)octan-3-one

There total 9 articles about rel-(1R,5S,6R,8S)-6-acetoxy-8-((1S)-1-acetoxy-2-p-toluenesulfonyloxyethyl)bicyclo(3.3.0)octan-3-one 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: 73.5%

: 109387-11-3
rel-(1R,5S,6R,8S)-6-acetoxy-8-((1S)-1-acetoxy-2-p-toluenesulfonyloxyethyl)bicyclo(3.3.0)octan-3-one, 2,2-dimethyltrimethylene acetal

: 109387-12-4
rel-(1R,5S,6R,8S)-6-acetoxy-8-((1S)-1-acetoxy-2-p-toluenesulfonyloxyethyl)bicyclo(3.3.0)octan-3-one

Guidance literature:: With toluene-4-sulfonic acid; In acetone; for 120h; Ambient temperature;
DOI:10.1016/S0040-4020(01)87331-2

Reference yield:

: 31824-15-4
Deslongchamps's diketone

: 109387-12-4
rel-(1R,5S,6R,8S)-6-acetoxy-8-((1S)-1-acetoxy-2-p-toluenesulfonyloxyethyl)bicyclo(3.3.0)octan-3-one

Guidance literature:: Multi-step reaction with 8 steps

1: TsOH / benzene

2: n-BuLi, i-Pr₂-NH / hexane; tetrahydrofuran / 1h, room temperature then 15min at room temperature

3: 66 percent / 85percent MCPBA, triethylammonium fluoride / CH₂Cl₂

4: 81 percent / pyridine / Ambient temperature

5: 1.) Li₂CO₃, 85percent MCPBA, 1,6-di-tert-butyl-4-methylphenol; 2.) 1M NaOH / 1.) dichloromethane, reflux, 36h; 2.) THF, 3d

6: LiAlH₄, sodium potassium tartrate / tetrahydrofuran; diethyl ether

7: 1.) pyridine; 2.) pyridine / 1.) dichloromethane, -4 degC, 2d; 2.) room temperature, 36h

8: 73.5 percent / p-toluenesulfonic acid / acetone / 120 h / Ambient temperature

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 1,6-di-t-butyl-4-methylphenol; lithium carbonate; Rochelle's salt; toluene-4-sulfonic acid; triethylamine hydrofluoride; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetone; benzene;
DOI:10.1016/S0040-4020(01)87331-2

Reference yield:

: C₁₈H₃₀O₄Si

: 109387-12-4
rel-(1R,5S,6R,8S)-6-acetoxy-8-((1S)-1-acetoxy-2-p-toluenesulfonyloxyethyl)bicyclo(3.3.0)octan-3-one

Guidance literature:: Multi-step reaction with 6 steps

1: 66 percent / 85percent MCPBA, triethylammonium fluoride / CH₂Cl₂

2: 81 percent / pyridine / Ambient temperature

3: 1.) Li₂CO₃, 85percent MCPBA, 1,6-di-tert-butyl-4-methylphenol; 2.) 1M NaOH / 1.) dichloromethane, reflux, 36h; 2.) THF, 3d

4: LiAlH₄, sodium potassium tartrate / tetrahydrofuran; diethyl ether

5: 1.) pyridine; 2.) pyridine / 1.) dichloromethane, -4 degC, 2d; 2.) room temperature, 36h

6: 73.5 percent / p-toluenesulfonic acid / acetone / 120 h / Ambient temperature

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; 1,6-di-t-butyl-4-methylphenol; lithium carbonate; Rochelle's salt; toluene-4-sulfonic acid; triethylamine hydrofluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;
DOI:10.1016/S0040-4020(01)87331-2