Methyl endo-11-acetoxy-8-(2-benzyloxycarbonylethyl)-exo-3,4-epoxy-5,5-ethylenedioxy-exo-2-methoxy-7-oxotricyclo<7.2.1.0^4,10>dodecane-8-carboxylate

Base Information

• Chemical Name: Methyl endo-11-acetoxy-8-(2-benzyloxycarbonylethyl)-exo-3,4-epoxy-5,5-ethylenedioxy-exo-2-methoxy-7-oxotricyclo<7.2.1.0^4,10>dodecane-8-carboxylate
• CAS No.: 141816-51-5
• Molecular Formula: C₂₉H₃₄O₁₁
• Molecular Weight: 558.582

Synonyms:Methyl endo-11-acetoxy-8-(2-benzyloxycarbonylethyl)-exo-3,4-epoxy-5,5-ethylenedioxy-exo-2-methoxy-7-oxotricyclo<7.2.1.0^4,10>dodecane-8-carboxylate

Chemical Property of Methyl endo-11-acetoxy-8-(2-benzyloxycarbonylethyl)-exo-3,4-epoxy-5,5-ethylenedioxy-exo-2-methoxy-7-oxotricyclo<7.2.1.0^4,10>dodecane-8-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl endo-11-acetoxy-8-(2-benzyloxycarbonylethyl)-exo-3,4-epoxy-5,5-ethylenedioxy-exo-2-methoxy-7-oxotricyclo<7.2.1.0^4,10>dodecane-8-carboxylate

There total 7 articles about Methyl endo-11-acetoxy-8-(2-benzyloxycarbonylethyl)-exo-3,4-epoxy-5,5-ethylenedioxy-exo-2-methoxy-7-oxotricyclo<7.2.1.0^4,10>dodecane-8-carboxylate 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: 75.0%

benzylacrylate (2495-35-4,25036-21-9) + Methyl endo-11-acetoxy-exo-3,4-epoxy-5,5-ethylenedioxy-exo-2-methoxy-7-oxotricyclo<7.2.1.04,10>dodecane-8-carboxylate (141816-44-6,141899-62-9) → Methyl endo-11-acetoxy-8-(2-benzyloxycarbonylethyl)-exo-3,4-epoxy-5,5-ethylenedioxy-exo-2-methoxy-7-oxotricyclo<7.2.1.04,10>dodecane-8-carboxylate (141816-51-5)

Guidance literature:

With potassium tert-butylate; tert-butyl alcohol; In 1,2-dimethoxyethane; for 20h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88535-5

Reference yield:

C18H22O6 (110129-73-2,141899-60-7) → Methyl endo-11-acetoxy-8-(2-benzyloxycarbonylethyl)-exo-3,4-epoxy-5,5-ethylenedioxy-exo-2-methoxy-7-oxotricyclo<7.2.1.04,10>dodecane-8-carboxylate (141816-51-5)

Guidance literature:

Multi-step reaction with 7 steps

1: CrO₃, pyridine / CH₂Cl₂ / 4 h / -20 °C

2: 56 percent / NaBH₄ / methanol / 0.5 h / 0 °C

3: 100 percent / CF₃CO₃H, K₂HPO₄ / CH₂Cl₂ / 1 h / Heating

4: Ag₂O, CaSO₄ / 24 h / Heating

5: 27 percent / tert-butanol, Li, liquid NH₃ / tetrahydrofuran / 0 h / -78 °C

6: 100 percent / DMSO, dicyclohexylcarbodiimide, pyridinium trifluoroacetate / benzene / 24 h / Ambient temperature

7: 75 percent / t-BuOK, t-BuOH / 1,2-dimethoxy-ethane / 20 h / Ambient temperature

With pyridine; chromium(VI) oxide; calcium sulfate; sodium tetrahydroborate; dipotassium hydrogenphosphate; trifluoroacetyl peroxide; potassium tert-butylate; ammonia; pyridinium trifluroacetate; lithium; dimethyl sulfoxide; dicyclohexyl-carbodiimide; silver(l) oxide; tert-butyl alcohol; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)88535-5

Reference yield:

Methyl endo-11-acetoxy-5,5-ethylenedioxy-2-oxotricyclo<7.2.1.04,10>dodeca-3,7-diene-8-carboxylate (141816-46-8) → Methyl endo-11-acetoxy-8-(2-benzyloxycarbonylethyl)-exo-3,4-epoxy-5,5-ethylenedioxy-exo-2-methoxy-7-oxotricyclo<7.2.1.04,10>dodecane-8-carboxylate (141816-51-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 56 percent / NaBH₄ / methanol / 0.5 h / 0 °C

2: 100 percent / CF₃CO₃H, K₂HPO₄ / CH₂Cl₂ / 1 h / Heating

3: Ag₂O, CaSO₄ / 24 h / Heating

4: 27 percent / tert-butanol, Li, liquid NH₃ / tetrahydrofuran / 0 h / -78 °C

5: 100 percent / DMSO, dicyclohexylcarbodiimide, pyridinium trifluoroacetate / benzene / 24 h / Ambient temperature

6: 75 percent / t-BuOK, t-BuOH / 1,2-dimethoxy-ethane / 20 h / Ambient temperature

With calcium sulfate; sodium tetrahydroborate; dipotassium hydrogenphosphate; trifluoroacetyl peroxide; potassium tert-butylate; ammonia; pyridinium trifluroacetate; lithium; dimethyl sulfoxide; dicyclohexyl-carbodiimide; silver(l) oxide; tert-butyl alcohol; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)88535-5

upstream raw materials:

benzylacrylate

Methyl endo-11-acetoxy-exo-3,4-epoxy-5,5-ethylenedioxy-exo-2-methoxy-7-oxotricyclo<7.2.1.0^4,10>dodecane-8-carboxylate

C₁₈H₂₂O₆

Methyl endo-11-acetoxy-5,5-ethylenedioxy-2-oxotricyclo<7.2.1.0^4,10>dodeca-3,7-diene-8-carboxylate

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