(1R,2S,3S,6R,8R,11S)-2,3-Dihydroxy-11-isopropenyl-5,6-dimethyl-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.0^2,6]undec-4-en-10-one

Base Information

• Chemical Name: (1R,2S,3S,6R,8R,11S)-2,3-Dihydroxy-11-isopropenyl-5,6-dimethyl-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.0^2,6]undec-4-en-10-one
• CAS No.: 88567-30-0
• Molecular Formula: C₂₁H₂₄O₄S
• Molecular Weight: 372.485

Synonyms:(1R,2S,3S,6R,8R,11S)-2,3-Dihydroxy-11-isopropenyl-5,6-dimethyl-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.0^2,6]undec-4-en-10-one

Chemical Property of (1R,2S,3S,6R,8R,11S)-2,3-Dihydroxy-11-isopropenyl-5,6-dimethyl-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.0^2,6]undec-4-en-10-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3S,6R,8R,11S)-2,3-Dihydroxy-11-isopropenyl-5,6-dimethyl-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.0^2,6]undec-4-en-10-one

There total 17 articles about (1R,2S,3S,6R,8R,11S)-2,3-Dihydroxy-11-isopropenyl-5,6-dimethyl-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.0^2,6]undec-4-en-10-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:

(Z)-3-((2S,3aR,6aS)-6a-Methoxy-3a-methyl-4-oxo-hexahydro-cyclopenta[b]furan-2-yl)-acrylic acid methyl ester (81491-82-9,81521-16-6,88588-66-3,88588-67-4) → (1R,2S,3S,6R,8R,11S)-2,3-Dihydroxy-11-isopropenyl-5,6-dimethyl-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.02,6]undec-4-en-10-one (88567-30-0)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) cuprous iodide / 1.) THF, 0 deg C, 40 min; 2.) THF, -40 deg C, 30 min

2: 95 percent / 5percent HCl / methanol / Ambient temperature

3: 69 percent / Jones' reagent / acetone / 1 h / 0 °C

4: 28 percent / sodium borohydride / ethanol; propan-2-ol; methanol / 2 h / -78 °C

5: 88 percent / imidazole / dimethylformamide / 15 h / 40 °C

6: 91 percent / potassium tert-butoxide / tetrahydrofuran; dimethylformamide / 1.) 0 deg C, 30 min; 2.) room temperature, 15 h

7: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

8: 92 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / Heating

10: 1.) dimethylsulfinyl carbanion / 1.) THF, DMSO, 20 min; 2.) THF, room temperature, 3.5 h

11: 85 percent / pyridinium p-toluenesulfonate / H₂O; tetrahydrofuran / 24 h / Ambient temperature

12: pyridine

13: 77 percent / vanadyloxy acetylacetonate, 70percent tert-butyl hydroperoxide / benzene / 1.5 h / Ambient temperature

14: 1.) n-butyllithium / 1.) hexane, benzene, room temperature, 1 h; 2.) benzene, room temperature, 3 h

15: 90 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / Ambient temperature

16: 1.) 0.5N NaOH; 2.) triethylamine, 2,4,6-trichlorobenzoyl chloride / 1.) methanol, reflux, 8 h; 2.) toluene, reflux, 4.5 h

With 1H-imidazole; hydrogenchloride; tert.-butylhydroperoxide; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; jones' reagent; bis(acetylacetonate)oxovanadium; dimethyl sulfoxide; deprotonated form; 2,4,6-trichlorobenzoyl chloride; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; benzene;

Reference yield:

(3aS,4R,5S,6R,7aR)-3a,6-Dihydroxy-5-isopropenyl-7a-methyl-1-methylene-3a,4,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid methyl ester (81492-00-4) → (1R,2S,3S,6R,8R,11S)-2,3-Dihydroxy-11-isopropenyl-5,6-dimethyl-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.02,6]undec-4-en-10-one (88567-30-0)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine

2: 77 percent / vanadyloxy acetylacetonate, 70percent tert-butyl hydroperoxide / benzene / 1.5 h / Ambient temperature

3: 1.) n-butyllithium / 1.) hexane, benzene, room temperature, 1 h; 2.) benzene, room temperature, 3 h

4: 90 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / Ambient temperature

5: 1.) 0.5N NaOH; 2.) triethylamine, 2,4,6-trichlorobenzoyl chloride / 1.) methanol, reflux, 8 h; 2.) toluene, reflux, 4.5 h

With tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; bis(acetylacetonate)oxovanadium; 2,4,6-trichlorobenzoyl chloride; pyridinium p-toluenesulfonate; triethylamine; In pyridine; dichloromethane; benzene;

Reference yield:

(3aS,4R,5S,6R,7aR)-6-Acetoxy-3a-hydroxy-5-isopropenyl-7a-methyl-1-methylene-3a,4,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid methyl ester (88567-25-3) → (1R,2S,3S,6R,8R,11S)-2,3-Dihydroxy-11-isopropenyl-5,6-dimethyl-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.02,6]undec-4-en-10-one (88567-30-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / vanadyloxy acetylacetonate, 70percent tert-butyl hydroperoxide / benzene / 1.5 h / Ambient temperature

2: 1.) n-butyllithium / 1.) hexane, benzene, room temperature, 1 h; 2.) benzene, room temperature, 3 h

3: 90 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / Ambient temperature

4: 1.) 0.5N NaOH; 2.) triethylamine, 2,4,6-trichlorobenzoyl chloride / 1.) methanol, reflux, 8 h; 2.) toluene, reflux, 4.5 h

With tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; bis(acetylacetonate)oxovanadium; 2,4,6-trichlorobenzoyl chloride; pyridinium p-toluenesulfonate; triethylamine; In dichloromethane; benzene;

upstream raw materials:

(2S,3S,3aS,4R,5S,6R,7aR)-6-Acetoxy-3a-hydroxy-5-isopropenyl-7a-methyl-1-methylene-2-phenylsulfanyl-3-(tetrahydro-furan-2-yloxy)-octahydro-indene-4-carboxylic acid methyl ester

(3aS,4R,5S,6R,7aR)-3a,6-Dihydroxy-5-isopropenyl-7a-methyl-1-methylene-3a,4,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid methyl ester

(3aS,4R,5S,6R,7aR)-6-Acetoxy-3a-hydroxy-5-isopropenyl-7a-methyl-1-methylene-3a,4,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid methyl ester

(1aS,1bR,2S,3R,4S,5aS,6aS)-4-Acetoxy-1b-hydroxy-3-isopropenyl-5a-methyl-6-methylene-octahydro-1-oxa-cyclopropa[a]indene-2-carboxylic acid methyl ester

Downstream raw materials:

C₂₁H₂₃BrO₄S

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