methyl (1R,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate

Base Information

• Chemical Name: methyl (1R,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate
• CAS No.: 945607-52-3
• Molecular Formula: C₂₂H₂₄O₅
• Molecular Weight: 368.43
• Mol file: 945607-52-3.mol

Synonyms:methyl (1R,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate

Chemical Property of methyl (1R,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1R,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate

There total 1 articles about methyl (1R,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-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: 82.0%

methyl (2S,3aR,4R,7S,7aS,9R)-9-(benzoyloxy)-2,3,3a,4,7,7a-hexahydro-2,4-dimethyl-8-oxo-4,7-ethano-1H-indene-2-carboxylate (914089-11-5) → methyl (1R,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate (945607-52-3) + methyl (1S,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate (914089-12-6) + methyl (2aR,4aR,6S,7aR,7bS)-1-(benzoyloxy)-1,2a,4a,5,6,7,7a,7b-octahydro-6,7-dimethyl-2-oxo-2H-cyclobut[e]indene-6-carboxylate

Guidance literature:

With acetophenone; In acetone; for 80h; UV-irradiation; cooling;

DOI:10.1016/j.tet.2007.03.073

Reference yield: 97.0%

methyl (1R,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate (945607-52-3) → methyl (1S,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate (914089-12-6)

Guidance literature:

With acetophenone; In acetone; for 36h; UV-irradiation; cooling;

DOI:10.1016/j.tet.2007.03.073

Reference yield:

methyl (1R,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate (945607-52-3) → methyl (2S,2aR,2bS,4S,5aR,6S,6aR)-decahydro-4,6-dimethyl-2-[(4-nitrobenzoyl)oxy]-2,6-methanocyclobuta[a]pentalene-4-carboxylate

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / acetophenone / acetone / 36 h / UV-irradiation; cooling

2: 25 percent / SmI₂ / tetrahydrofuran; methanol / -78 - 18 °C

3: 75 percent / 4-(N,N-dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 3 h / 18 °C

With dmap; samarium diiodide; triethylamine; acetophenone; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1016/j.tet.2007.03.073

upstream raw materials:

methyl (2S,3aR,4R,7S,7aS,9R)-9-(benzoyloxy)-2,3,3a,4,7,7a-hexahydro-2,4-dimethyl-8-oxo-4,7-ethano-1H-indene-2-carboxylate

Downstream raw materials:

methyl (1S,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate

(1S,2R,4S,6R,8S,9S)-8,9-epoxy-1,4-dimethyl-11-methylene-10-oxotricyclo<6.3.0.0^2,6>undecane-4-carboxylic acid

(+)-hirsutic acid

methyl [2S-(2α,3aα,3bβ,7aα)]-2,3,3a,3b,4,5,7,7a-octahydro-2,3b,4-trimethyl-5-oxo-4-(phenylseleno)-1H-cyclopenta[a]pentalene-2-carboxylate