Acetic acid (1R,2S,3S,4S,6R,8R,11S)-3-acetoxy-11-isopropenyl-6-methyl-5-methylene-10-oxo-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.0^2,6]undec-2-yl ester

Base Information

• Chemical Name: Acetic acid (1R,2S,3S,4S,6R,8R,11S)-3-acetoxy-11-isopropenyl-6-methyl-5-methylene-10-oxo-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.0^2,6]undec-2-yl ester
• CAS No.: 88593-68-4
• Molecular Formula: C₂₅H₂₈O₆S
• Molecular Weight: 456.56

Synonyms:

Chemical Property of Acetic acid (1R,2S,3S,4S,6R,8R,11S)-3-acetoxy-11-isopropenyl-6-methyl-5-methylene-10-oxo-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.0^2,6]undec-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,2S,3S,4S,6R,8R,11S)-3-acetoxy-11-isopropenyl-6-methyl-5-methylene-10-oxo-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.0^2,6]undec-2-yl ester

There total 17 articles about Acetic acid (1R,2S,3S,4S,6R,8R,11S)-3-acetoxy-11-isopropenyl-6-methyl-5-methylene-10-oxo-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.0^2,6]undec-2-yl ester 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: 26.0%

acetic anhydride (108-24-7) + (1R,2S,3S,4S,6R,8R,11S)-2,3-Dihydroxy-11-isopropenyl-6-methyl-5-methylene-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.02,6]undecan-10-one → Acetic acid (1R,2S,3S,4S,6R,8R,11S)-2-hydroxy-11-isopropenyl-6-methyl-5-methylene-10-oxo-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.02,6]undec-3-yl ester (88567-33-3) + Acetic acid (1R,2S,3S,4S,6R,8R,11S)-3-acetoxy-11-isopropenyl-6-methyl-5-methylene-10-oxo-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.02,6]undec-2-yl ester (88593-68-4)

Guidance literature:

In toluene; for 2h; Heating;

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) → Acetic acid (1R,2S,3S,4S,6R,8R,11S)-3-acetoxy-11-isopropenyl-6-methyl-5-methylene-10-oxo-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.02,6]undec-2-yl ester (88593-68-4)

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: potassium carbonate / H₂O; methanol / 2 h / 90 °C

16: 26 percent / toluene / 2 h / Heating

With 1H-imidazole; hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; jones' reagent; bis(acetylacetonate)oxovanadium; dimethyl sulfoxide; deprotonated form; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium carbonate; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; 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) → Acetic acid (1R,2S,3S,4S,6R,8R,11S)-3-acetoxy-11-isopropenyl-6-methyl-5-methylene-10-oxo-4-phenylsulfanyl-9-oxa-tricyclo[6.2.1.02,6]undec-2-yl ester (88593-68-4)

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: potassium carbonate / H₂O; methanol / 2 h / 90 °C

5: 26 percent / toluene / 2 h / Heating

With tert.-butylhydroperoxide; n-butyllithium; bis(acetylacetonate)oxovanadium; potassium carbonate; In pyridine; methanol; water; toluene; benzene;

upstream raw materials:

acetic anhydride

(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

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