(S)-3-Cyclohexylidene-4-(1-methoxy-1-methyl-ethyl)-cyclopentane-1,1-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (S)-3-Cyclohexylidene-4-(1-methoxy-1-methyl-ethyl)-cyclopentane-1,1-dicarboxylic acid dimethyl ester
• CAS No.: 213531-63-6
• Molecular Formula: C₁₉H₃₀O₅
• Molecular Weight: 338.444

Synonyms:(S)-3-Cyclohexylidene-4-(1-methoxy-1-methyl-ethyl)-cyclopentane-1,1-dicarboxylic acid dimethyl ester

Chemical Property of (S)-3-Cyclohexylidene-4-(1-methoxy-1-methyl-ethyl)-cyclopentane-1,1-dicarboxylic acid dimethyl ester

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Technology Process of (S)-3-Cyclohexylidene-4-(1-methoxy-1-methyl-ethyl)-cyclopentane-1,1-dicarboxylic acid dimethyl ester

There total 3 articles about (S)-3-Cyclohexylidene-4-(1-methoxy-1-methyl-ethyl)-cyclopentane-1,1-dicarboxylic acid dimethyl 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:

2-[2-Cyclohexylidene-2-((S)-toluene-4-sulfinyl)-ethyl]-2-(3-methoxy-3-methyl-2-phenylselanyl-butyl)-malonic acid dimethyl ester (213531-58-9) → (S)-3-Cyclohexylidene-4-(1-methoxy-1-methyl-ethyl)-cyclopentane-1,1-dicarboxylic acid dimethyl ester (213531-63-6) + (R)-3-Cyclohexylidene-4-(1-methoxy-1-methyl-ethyl)-cyclopentane-1,1-dicarboxylic acid dimethyl ester

Guidance literature:

With triethyl borane; oxygen; tri-n-butyl-tin hydride; In toluene; at -40 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1002/(SICI)1521-3773(19980817)37:15<2116::AID-ANIE2116>3.0.CO;2-L

Reference yield:

(S)-2-bromo-1-cyclohexylidene-1-p-tolylsulfinyl ethane (152836-38-9) → (S)-3-Cyclohexylidene-4-(1-methoxy-1-methyl-ethyl)-cyclopentane-1,1-dicarboxylic acid dimethyl ester (213531-63-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran

2: Bu₃SnH; triethylborane; O₂ / toluene / -40 °C

With triethyl borane; oxygen; tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; toluene; 1: Substitution / 2: Cyclization;

DOI:10.1021/ja992818u

Reference yield:

2-(3-Methoxy-3-methyl-2-phenylselanyl-butyl)-malonic acid dimethyl ester → (S)-3-Cyclohexylidene-4-(1-methoxy-1-methyl-ethyl)-cyclopentane-1,1-dicarboxylic acid dimethyl ester (213531-63-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran

2: Bu₃SnH; triethylborane; O₂ / toluene / -40 °C

With triethyl borane; oxygen; tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; toluene; 1: Substitution / 2: Cyclization;

DOI:10.1021/ja992818u

upstream raw materials:

2-[2-Cyclohexylidene-2-((S)-toluene-4-sulfinyl)-ethyl]-2-(3-methoxy-3-methyl-2-phenylselanyl-butyl)-malonic acid dimethyl ester

(S)-2-bromo-1-cyclohexylidene-1-p-tolylsulfinyl ethane

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