(1S,3aR,6R,6aR)-6-Acetyl-1-benzyloxy-3-methylene-octahydro-pentalene-1-carboxylic acid methyl ester

Base Information

• Chemical Name: (1S,3aR,6R,6aR)-6-Acetyl-1-benzyloxy-3-methylene-octahydro-pentalene-1-carboxylic acid methyl ester
• CAS No.: 172996-19-9
• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.408

Synonyms:(1S,3aR,6R,6aR)-6-Acetyl-1-benzyloxy-3-methylene-octahydro-pentalene-1-carboxylic acid methyl ester

Chemical Property of (1S,3aR,6R,6aR)-6-Acetyl-1-benzyloxy-3-methylene-octahydro-pentalene-1-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3aR,6R,6aR)-6-Acetyl-1-benzyloxy-3-methylene-octahydro-pentalene-1-carboxylic acid methyl ester

There total 13 articles about (1S,3aR,6R,6aR)-6-Acetyl-1-benzyloxy-3-methylene-octahydro-pentalene-1-carboxylic acid methyl 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:

(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone (61305-35-9) → (1S,3aR,6R,6aR)-6-Acetyl-1-benzyloxy-3-methylene-octahydro-pentalene-1-carboxylic acid methyl ester (172996-19-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / CuBr-Me₂S complex, HMPA / tetrahydrofuran / 1 h / -78 °C

2: 1.) MeLi / 1.) THF, -20 deg C, 0.5 h, 2.) THF, -20 deg, overnight

3: 87 percent / triethylamine, triphenylphosphine, palladium acetate / dimethylformamide / 3 h / 760 Torr

4: 85 percent / p-toluenesulfonic acid / acetone / 36 h / Ambient temperature

5: 1). potasium tert-butoxide 2.)K₂CO₃ / 1.) benzene, RT, 10 min, 2.) MeOH, overnight

6: 93 percent / p-toluenesulfonic acid, pyridine / methanol / 8 h

7: 1.) N-methylomorpholine N-oxide, N-methylmorpholine, 4 Angstroem molecular sieves , 2.) tetrapropylamoniumperruthenate / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, overnight

8: LDA / tetrahydrofuran

9: NBS, propylene oxide, Et₃N

10: 78 percent / 30percent H₂O₂, 1 N NaOH / CH₂Cl₂; methanol / 2 h / -10 - 10 °C

11: 1). 1.3 M n-butyllithium / 1). THF, RT, 0.5 h, 2). THF, from -78 deg C to RT, 6 h

12: amonium formate, Pd₂(dba)3*CHCl₃, tributylphosphine / dioxane / 1 h / Heating

13: 1.) tetrabutylammonium iodide, sodium hydride, 2.) p-toluenosulfonic acid / 1.) DMF, 15 min., 2.) acetone, 5 min.,

With 4-methyl-morpholine; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; N-Bromosuccinimide; tetrapropylammonium perruthennate; tributylphosphine; 4 A molecular sieve; potassium tert-butylate; methyllithium; dihydrogen peroxide; ammonium formate; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; methyloxirane; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja9533454

Reference yield:

3-(2-methyl-1,3-dioxolan-2-yl)prop-1-yl magnesium bromide → (1S,3aR,6R,6aR)-6-Acetyl-1-benzyloxy-3-methylene-octahydro-pentalene-1-carboxylic acid methyl ester (172996-19-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / CuBr-Me₂S complex, HMPA / tetrahydrofuran / 1 h / -78 °C

2: 1.) MeLi / 1.) THF, -20 deg C, 0.5 h, 2.) THF, -20 deg, overnight

3: 87 percent / triethylamine, triphenylphosphine, palladium acetate / dimethylformamide / 3 h / 760 Torr

4: 85 percent / p-toluenesulfonic acid / acetone / 36 h / Ambient temperature

5: 1). potasium tert-butoxide 2.)K₂CO₃ / 1.) benzene, RT, 10 min, 2.) MeOH, overnight

6: 93 percent / p-toluenesulfonic acid, pyridine / methanol / 8 h

7: 1.) N-methylomorpholine N-oxide, N-methylmorpholine, 4 Angstroem molecular sieves , 2.) tetrapropylamoniumperruthenate / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, overnight

8: LDA / tetrahydrofuran

9: NBS, propylene oxide, Et₃N

10: 78 percent / 30percent H₂O₂, 1 N NaOH / CH₂Cl₂; methanol / 2 h / -10 - 10 °C

11: 1). 1.3 M n-butyllithium / 1). THF, RT, 0.5 h, 2). THF, from -78 deg C to RT, 6 h

12: amonium formate, Pd₂(dba)3*CHCl₃, tributylphosphine / dioxane / 1 h / Heating

13: 1.) tetrabutylammonium iodide, sodium hydride, 2.) p-toluenosulfonic acid / 1.) DMF, 15 min., 2.) acetone, 5 min.,

With 4-methyl-morpholine; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; N-Bromosuccinimide; tetrapropylammonium perruthennate; tributylphosphine; 4 A molecular sieve; potassium tert-butylate; methyllithium; dihydrogen peroxide; ammonium formate; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; methyloxirane; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja9533454

Reference yield:

methyl (1S,3aR,6R,6aR)-6-(1,1-dimethoxyethyl)octahydro-3-oxo-1-pentalenecarboxylate (172996-05-3) → (1S,3aR,6R,6aR)-6-Acetyl-1-benzyloxy-3-methylene-octahydro-pentalene-1-carboxylic acid methyl ester (172996-19-9)

Guidance literature:

Multi-step reaction with 6 steps

1: LDA / tetrahydrofuran

2: NBS, propylene oxide, Et₃N

3: 78 percent / 30percent H₂O₂, 1 N NaOH / CH₂Cl₂; methanol / 2 h / -10 - 10 °C

4: 1). 1.3 M n-butyllithium / 1). THF, RT, 0.5 h, 2). THF, from -78 deg C to RT, 6 h

5: amonium formate, Pd₂(dba)3*CHCl₃, tributylphosphine / dioxane / 1 h / Heating

6: 1.) tetrabutylammonium iodide, sodium hydride, 2.) p-toluenosulfonic acid / 1.) DMF, 15 min., 2.) acetone, 5 min.,

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; N-Bromosuccinimide; tributylphosphine; dihydrogen peroxide; ammonium formate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; methyloxirane; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/ja9533454

upstream raw materials:

benzyl bromide

(1S,3aR,6R,6aR)-6-(1,1-Dimethoxy-ethyl)-1-hydroxy-3-methylene-octahydro-pentalene-1-carboxylic acid methyl ester

(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone

methyl (1S,3aR,6R,6aR)-6-(1,1-dimethoxyethyl)octahydro-3-oxo-1-pentalenecarboxylate

Downstream raw materials:

(3S,3aR,5aR,7aS,7bR)-7a-Benzyloxy-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-cyclopent-1-enyl]-3-methyl-6-methylene-octahydro-pentaleno[1,6-cd]pyran-1-one

(2aR,3R,4aS,6aR,8S,9aR,10S,10aR,10bS)-4a-(benzyloxy)-2a,4,4a,6a,7,10,10a,10b-octacahydro-7,7,10-trimethyl-10-hydroxyspiro[cyclopenta[5,6]cycloocta(1,2,3-cd)pentalene-3(1H),2'-oxirane]-5,8(2H,6H)-dione

(2aR,3R,4aS,6aR,8S,9aR,10S,10aR,10bS)-4a-(benzyloxy)-2a,4,4a,6a,7,10,10a,10b-octacahydro-7,7,10-trimethyl-10-hydroxyspiro[cyclopenta[5,6]cycloocta(1,2,3-cd)pentalene-3(1H),2'-oxirane]-5(2H,6H)-one

C₃₃H₅₂O₅Si

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