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

Base Information

• Chemical Name: 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
• CAS No.: 85757-82-0
• Molecular Formula: C₂₂H₂₆O₃Se
• Molecular Weight: 417.407
• Mol file: 85757-82-0.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 14 articles about 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 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:

Phenylselenyl chloride (5707-04-0) + methyl [2S-(2α,3aα,3bβ,7aα)]-2,3,3a,3b,4,5,7,7a-octahydro-2,3b,4-trimethyl-5-oxo-1H-cyclopenta[a]pentalene-2-carboxylate (85848-62-0) → 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 (85757-82-0)

Guidance literature:

methyl [2S-(2α,3aα,3bβ,7aα)]-2,3,3a,3b,4,5,7,7a-octahydro-2,3b,4-trimethyl-5-oxo-1H-cyclopenta[a]pentalene-2-carboxylate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

Phenylselenyl chloride; In tetrahydrofuran; at -78 - 18 ℃; for 0.75h; Further stages.;

DOI:10.1016/j.tet.2007.03.073

Reference yield:

methyl (2S,3aR,3bS,7aS)-2,3,3a,3b,4,5,7,7a-octahydro-2,3b-dimethyl-5-oxo-1H-cyclopentapentalene-2-carboxylate (85799-03-7) → 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 (85757-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran / 0.17 h / -78 °C

1.2: tetrahydrofuran / 1 h / 0 °C

2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

2.2: tetrahydrofuran / 0.75 h / -78 - 18 °C

With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/j.tet.2007.03.073

Reference yield:

methyl (1R,2S,5R,7S)-2,7-dimethyl-3-oxo-2-(2-oxopropyl)-cis-bicyclo<3.3.0>octane-7-carboxylate (85799-02-6) → 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 (85757-82-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / t-C₄H₉OK, t-C₄H₉OH

2: 85 percent / LDA / tetrahydrofuran / -78 - 0 °C

3: 1.) LDA / 1.) -78 deg C, 0.5h, 2.) -78 - 0 deg C

With potassium tert-butylate; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)85826-8

upstream raw materials:

Phenylselenyl bromide

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

Phenylselenyl chloride

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

Downstream raw materials:

(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